Preserve direct-serve redirects for blob HEAD requests

config.example.yaml

@@ -96,7 +96,8 @@ upstream:
   cargo_download: "https://static.crates.io/crates"
 
   # Authentication for upstream registries
-  # Keys are URL prefixes matched against request URLs.
+  # Keys are absolute URL scopes. Scheme, host, effective port, and path
+  # segment boundaries must match; the longest matching scope wins.
   # Values can reference environment variables using ${VAR_NAME} syntax.
   #
   # Supported auth types:

docs/architecture.md

@@ -240,6 +240,8 @@ Fetches artifacts from upstream registries.
 - Exponential backoff retry on 429 (rate limit) and 5xx errors
 - Returns streaming reader (doesn't load into memory)
 - Configurable user-agent
+- Shares an authentication-aware transport with metadata requests so URL-scoped credentials apply consistently
+- Discovers and caches scoped OCI Bearer tokens from registry challenges
 
 **Resolver:**
 - Determines download URL for a package/version
@@ -351,6 +353,7 @@ Eviction can be implemented as:
 - Fresh data - new versions visible immediately
 - Metadata is small, upstream fetch is fast
 - Set `cache_metadata: true` or use the mirror command to enable metadata caching for offline use via the `metadata_cache` table
+- OCI manifests are the exception: they are cached automatically so previously fetched images remain pullable when the registry or token service is unavailable
 
 **Why stream artifacts?**
 - Memory efficient - don't load large files into RAM

docs/configuration.md

@@ -123,7 +123,9 @@ upstream:
 
 ## Authentication
 
-Configure authentication for private upstream registries. Auth is matched by URL prefix, and credentials can reference environment variables using `${VAR_NAME}` syntax.
+Configure authentication for private upstream registries. The same authentication-aware client is used for metadata and artifact downloads, and credentials can reference environment variables using `${VAR_NAME}` syntax.
+
+OCI registries that return a Bearer challenge from a `/v2/{repository}/…` endpoint are handled automatically. The proxy discovers the token realm from `WWW-Authenticate`, applies any configured credentials for the token URL, and reuses the scoped token until shortly before it expires.
 
 ### Bearer Token
 
@@ -172,7 +174,7 @@ upstream:
 
 ### URL Matching
 
-Auth configs are matched by URL prefix. The longest matching prefix wins, so you can configure different credentials for different paths:
+Auth keys must be absolute URLs. Matching compares the scheme, host, effective port, and path-segment prefix, preventing credentials for `registry.example.com` from being sent to a lookalike host such as `registry.example.com.evil.test`. The longest matching scope wins, so you can configure different credentials for different paths:
 
 ```yaml
 upstream:
@@ -244,6 +246,8 @@ Note: Hex cooldown requires disabling registry signature verification since the
 
 By default the proxy fetches metadata fresh from upstream on every request. Enable `cache_metadata` to store metadata responses in the database and storage backend for offline fallback. When upstream is unreachable, the proxy serves the last cached copy. ETag-based revalidation avoids re-downloading unchanged metadata.
 
+OCI manifests are always cached because cached image blobs cannot be pulled without their manifests. Digest-addressed manifests are immutable and served directly from cache. Tag-addressed manifests follow `metadata_ttl`, revalidate when stale, and fall back to the last cached response when the registry is unavailable.
+
 ```yaml
 cache_metadata: true
 ```

internal/config/config.go

@@ -274,23 +274,29 @@ type UpstreamConfig struct {
 	CargoDownload string `json:"cargo_download" yaml:"cargo_download"`
 
 	// Auth configures authentication for upstream registries.
-	// Keys are URL prefixes that are matched against request URLs.
+	// Keys are absolute URL scopes matched by scheme, host, effective port,
+	// and path-segment prefix.
 	// Example: "https://npm.pkg.github.com" matches all requests to that host.
 	Auth map[string]AuthConfig `json:"auth" yaml:"auth"`
 }
 
 // AuthForURL returns the auth config that matches the given URL.
-// Matches are based on URL prefix - the longest matching prefix wins.
+// The longest matching URL scope wins.
 func (u *UpstreamConfig) AuthForURL(url string) *AuthConfig {
 	if u.Auth == nil {
 		return nil
 	}
+	target, err := parseAuthURL(url)
+	if err != nil {
+		return nil
+	}
 
 	var bestMatch *AuthConfig
 	var bestLen int
 
 	for pattern, auth := range u.Auth {
-		if strings.HasPrefix(url, pattern) && len(pattern) > bestLen {
+		configured, err := parseAuthURL(pattern)
+		if err == nil && authURLMatches(configured, target) && len(pattern) > bestLen {
 			a := auth // copy to avoid loop variable capture
 			bestMatch = &a
 			bestLen = len(pattern)
@@ -300,6 +306,45 @@ func (u *UpstreamConfig) AuthForURL(url string) *AuthConfig {
 	return bestMatch
 }
 
+func parseAuthURL(value string) (*url.URL, error) {
+	parsed, err := url.Parse(value)
+	if err != nil || !parsed.IsAbs() || parsed.Hostname() == "" || parsed.Opaque != "" {
+		return nil, fmt.Errorf("invalid authentication URL")
+	}
+	return parsed, nil
+}
+
+func authURLMatches(configured, target *url.URL) bool {
+	if !strings.EqualFold(configured.Scheme, target.Scheme) ||
+		!strings.EqualFold(configured.Hostname(), target.Hostname()) ||
+		authURLPort(configured) != authURLPort(target) {
+		return false
+	}
+	if configured.RawQuery != "" && configured.RawQuery != target.RawQuery {
+		return false
+	}
+
+	configuredPath := strings.TrimSuffix(configured.EscapedPath(), "/")
+	if configuredPath == "" {
+		return true
+	}
+	targetPath := strings.TrimSuffix(target.EscapedPath(), "/")
+	return targetPath == configuredPath || strings.HasPrefix(targetPath, configuredPath+"/")
+}
+
+func authURLPort(value *url.URL) string {
+	if port := value.Port(); port != "" {
+		return port
+	}
+	if strings.EqualFold(value.Scheme, "https") {
+		return "443"
+	}
+	if strings.EqualFold(value.Scheme, "http") {
+		return "80"
+	}
+	return ""
+}
+
 // AuthConfig configures authentication for an upstream registry.
 type AuthConfig struct {
 	// Type is the authentication type: "bearer", "basic", or "header".

internal/config/config_test.go

@@ -760,3 +760,45 @@ func TestDatabaseConfigString(t *testing.T) {
 		}
 	}
 }
+
+func TestUpstreamAuthForURLMatchesURLComponents(t *testing.T) {
+	registryAuth := AuthConfig{Type: "bearer", Token: "registry-token"}
+	privateAuth := AuthConfig{Type: "bearer", Token: "private-token"}
+	config := UpstreamConfig{Auth: map[string]AuthConfig{
+		"https://registry.example.com":         registryAuth,
+		"https://registry.example.com/private": privateAuth,
+	}}
+
+	tests := []struct {
+		name      string
+		url       string
+		wantToken string
+	}{
+		{name: "registry root", url: "https://registry.example.com/package", wantToken: "registry-token"},
+		{name: "host is case insensitive", url: "https://REGISTRY.EXAMPLE.COM/package", wantToken: "registry-token"},
+		{name: "longest path match", url: "https://registry.example.com/private/package", wantToken: "private-token"},
+		{name: "exact path match", url: "https://registry.example.com/private", wantToken: "private-token"},
+		{name: "path segment boundary", url: "https://registry.example.com/private-other/package", wantToken: "registry-token"},
+		{name: "lookalike host rejected", url: "https://registry.example.com.evil.test/package"},
+		{name: "different scheme rejected", url: "http://registry.example.com/package"},
+		{name: "different port rejected", url: "https://registry.example.com:8443/package"},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			auth := config.AuthForURL(tt.url)
+			if tt.wantToken == "" {
+				if auth != nil {
+					t.Fatalf("AuthForURL() = %+v, want nil", auth)
+				}
+				return
+			}
+			if auth == nil {
+				t.Fatal("AuthForURL() = nil, want authentication")
+			}
+			if auth.Token != tt.wantToken {
+				t.Errorf("token = %q, want %q", auth.Token, tt.wantToken)
+			}
+		})
+	}
+}

internal/database/metadata_cache_test.go

@@ -30,6 +30,10 @@ func TestUpsertAndGetMetadataCache(t *testing.T) {
 		StoragePath: "_metadata/npm/lodash/metadata",
 		ETag:        sql.NullString{String: `"abc123"`, Valid: true},
 		ContentType: sql.NullString{String: "application/json", Valid: true},
+		ContentDigest: sql.NullString{
+			String: "sha256:0123456789abcdef",
+			Valid:  true,
+		},
 		Size:      sql.NullInt64{Int64: 1024, Valid: true},
 		FetchedAt: sql.NullTime{Time: time.Now(), Valid: true},
 	}
@@ -62,6 +66,9 @@ func TestUpsertAndGetMetadataCache(t *testing.T) {
 	if !got.ContentType.Valid || got.ContentType.String != "application/json" {
 		t.Errorf("content_type = %v, want %q", got.ContentType, "application/json")
 	}
+	if !got.ContentDigest.Valid || got.ContentDigest.String != "sha256:0123456789abcdef" {
+		t.Errorf("content_digest = %v, want %q", got.ContentDigest, "sha256:0123456789abcdef")
+	}
 	if !got.Size.Valid || got.Size.Int64 != 1024 {
 		t.Errorf("size = %v, want 1024", got.Size)
 	}
@@ -178,3 +185,47 @@ func TestMetadataCacheTableCreatedByMigration(t *testing.T) {
 		t.Error("metadata_cache table should exist after migration")
 	}
 }
+
+func TestMetadataCacheContentDigestMigrationPreservesExistingRows(t *testing.T) {
+	dbPath := filepath.Join(t.TempDir(), "test.db")
+	db, err := Create(dbPath)
+	if err != nil {
+		t.Fatalf("Create failed: %v", err)
+	}
+	defer func() { _ = db.Close() }()
+
+	if _, err := db.Exec("ALTER TABLE metadata_cache DROP COLUMN content_digest"); err != nil {
+		t.Fatalf("dropping content_digest: %v", err)
+	}
+	if _, err := db.Exec("DELETE FROM migrations WHERE name = ?", "006_add_metadata_content_digest"); err != nil {
+		t.Fatalf("resetting digest migration: %v", err)
+	}
+	if _, err := db.Exec(`
+		INSERT INTO metadata_cache (ecosystem, name, storage_path, content_type, size, fetched_at, created_at, updated_at)
+		VALUES (?, ?, ?, ?, ?, ?, ?, ?)
+	`, "oci-manifest", "cache-key", "_metadata/oci-manifest/cache-key/metadata", "application/json", 2, time.Now(), time.Now(), time.Now()); err != nil {
+		t.Fatalf("inserting legacy cache row: %v", err)
+	}
+
+	if err := db.MigrateSchema(); err != nil {
+		t.Fatalf("MigrateSchema() error = %v", err)
+	}
+	hasDigest, err := db.HasColumn("metadata_cache", "content_digest")
+	if err != nil {
+		t.Fatalf("HasColumn() error = %v", err)
+	}
+	if !hasDigest {
+		t.Fatal("metadata_cache.content_digest was not added")
+	}
+
+	entry, err := db.GetMetadataCache("oci-manifest", "cache-key")
+	if err != nil {
+		t.Fatalf("GetMetadataCache() error = %v", err)
+	}
+	if entry == nil || entry.StoragePath != "_metadata/oci-manifest/cache-key/metadata" {
+		t.Fatalf("existing metadata cache row was not preserved: %#v", entry)
+	}
+	if entry.ContentDigest.Valid {
+		t.Errorf("legacy content digest = %q, want NULL", entry.ContentDigest.String)
+	}
+}

internal/database/queries.go

@@ -894,7 +894,7 @@ func (db *DB) GetMetadataCache(ecosystem, name string) (*MetadataCacheEntry, err
 	var entry MetadataCacheEntry
 	query := db.Rebind(`
 		SELECT id, ecosystem, name, storage_path, etag, content_type,
-		       size, last_modified, fetched_at, created_at, updated_at
+		       content_digest, size, last_modified, fetched_at, created_at, updated_at
 		FROM metadata_cache WHERE ecosystem = ? AND name = ?
 	`)
 	err := db.Get(&entry, query, ecosystem, name)
@@ -914,12 +914,13 @@ func (db *DB) UpsertMetadataCache(entry *MetadataCacheEntry) error {
 	if db.dialect == DialectPostgres {
 		query = `
 			INSERT INTO metadata_cache (ecosystem, name, storage_path, etag, content_type,
-			                            size, last_modified, fetched_at, created_at, updated_at)
-			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9, $10)
+			                            content_digest, size, last_modified, fetched_at, created_at, updated_at)
+			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11)
 			ON CONFLICT(ecosystem, name) DO UPDATE SET
 				storage_path = EXCLUDED.storage_path,
 				etag = EXCLUDED.etag,
 				content_type = EXCLUDED.content_type,
+				content_digest = EXCLUDED.content_digest,
 				size = EXCLUDED.size,
 				last_modified = EXCLUDED.last_modified,
 				fetched_at = EXCLUDED.fetched_at,
@@ -928,12 +929,13 @@ func (db *DB) UpsertMetadataCache(entry *MetadataCacheEntry) error {
 	} else {
 		query = `
 			INSERT INTO metadata_cache (ecosystem, name, storage_path, etag, content_type,
-			                            size, last_modified, fetched_at, created_at, updated_at)
-			VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
+			                            content_digest, size, last_modified, fetched_at, created_at, updated_at)
+			VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
 			ON CONFLICT(ecosystem, name) DO UPDATE SET
 				storage_path = excluded.storage_path,
 				etag = excluded.etag,
 				content_type = excluded.content_type,
+				content_digest = excluded.content_digest,
 				size = excluded.size,
 				last_modified = excluded.last_modified,
 				fetched_at = excluded.fetched_at,
@@ -943,7 +945,7 @@ func (db *DB) UpsertMetadataCache(entry *MetadataCacheEntry) error {
 
 	_, err := db.Exec(query,
 		entry.Ecosystem, entry.Name, entry.StoragePath, entry.ETag,
-		entry.ContentType, entry.Size, entry.LastModified, entry.FetchedAt, now, now,
+		entry.ContentType, entry.ContentDigest, entry.Size, entry.LastModified, entry.FetchedAt, now, now,
 	)
 	if err != nil {
 		return fmt.Errorf("upserting metadata cache: %w", err)

internal/database/schema.go

@@ -102,6 +102,7 @@ CREATE TABLE IF NOT EXISTS metadata_cache (
 	storage_path TEXT NOT NULL,
 	etag TEXT,
 	content_type TEXT,
+	content_digest TEXT,
 	size INTEGER,
 	last_modified DATETIME,
 	fetched_at DATETIME,
@@ -202,6 +203,7 @@ CREATE TABLE IF NOT EXISTS metadata_cache (
 	storage_path TEXT NOT NULL,
 	etag TEXT,
 	content_type TEXT,
+	content_digest TEXT,
 	size BIGINT,
 	last_modified TIMESTAMP,
 	fetched_at TIMESTAMP,
@@ -359,6 +361,7 @@ var migrations = []migration{
 	{"003_ensure_artifacts_table", migrateEnsureArtifactsTable},
 	{"004_ensure_vulnerabilities_table", migrateEnsureVulnerabilitiesTable},
 	{"005_ensure_metadata_cache_table", migrateEnsureMetadataCacheTable},
+	{"006_add_metadata_content_digest", migrateAddMetadataContentDigest},
 }
 
 // isTableNotFound returns true if the error indicates a missing table.
@@ -581,6 +584,20 @@ func migrateEnsureMetadataCacheTable(db *DB) error {
 	return db.EnsureMetadataCacheTable()
 }
 
+func migrateAddMetadataContentDigest(db *DB) error {
+	hasColumn, err := db.HasColumn("metadata_cache", "content_digest")
+	if err != nil {
+		return fmt.Errorf("checking metadata_cache content_digest column: %w", err)
+	}
+	if hasColumn {
+		return nil
+	}
+	if _, err := db.Exec("ALTER TABLE metadata_cache ADD COLUMN content_digest TEXT"); err != nil {
+		return fmt.Errorf("adding metadata_cache content_digest column: %w", err)
+	}
+	return nil
+}
+
 // EnsureMetadataCacheTable creates the metadata_cache table if it doesn't exist.
 func (db *DB) EnsureMetadataCacheTable() error {
 	has, err := db.HasTable("metadata_cache")
@@ -601,6 +618,7 @@ func (db *DB) EnsureMetadataCacheTable() error {
 				storage_path TEXT NOT NULL,
 				etag TEXT,
 				content_type TEXT,
+				content_digest TEXT,
 				size BIGINT,
 				last_modified TIMESTAMP,
 				fetched_at TIMESTAMP,
@@ -618,6 +636,7 @@ func (db *DB) EnsureMetadataCacheTable() error {
 				storage_path TEXT NOT NULL,
 				etag TEXT,
 				content_type TEXT,
+				content_digest TEXT,
 				size INTEGER,
 				last_modified DATETIME,
 				fetched_at DATETIME,

internal/database/types.go

@@ -84,6 +84,7 @@ type MetadataCacheEntry struct {
 	StoragePath   string         `db:"storage_path" json:"storage_path"`
 	ETag          sql.NullString `db:"etag" json:"etag,omitempty"`
 	ContentType   sql.NullString `db:"content_type" json:"content_type,omitempty"`
+	ContentDigest sql.NullString `db:"content_digest" json:"content_digest,omitempty"`
 	Size          sql.NullInt64  `db:"size" json:"size,omitempty"`
 	LastModified  sql.NullTime   `db:"last_modified" json:"last_modified,omitempty"`
 	FetchedAt     sql.NullTime   `db:"fetched_at" json:"fetched_at,omitempty"`

internal/handler/container.go

@@ -11,7 +11,6 @@ import (
 
 const (
 	dockerHubRegistry  = "https://registry-1.docker.io"
-	dockerHubAuth      = "https://auth.docker.io"
 	blobMatchCount     = 3 // full match + name + digest
 	manifestMatchCount = 3 // full match + name + reference
 	tagsListMatchCount = 2 // full match + name
@@ -23,7 +22,6 @@ const (
 type ContainerHandler struct {
 	proxy       *Proxy
 	registryURL string
-	authURL     string
 	proxyURL    string
 }
 
@@ -32,7 +30,6 @@ func NewContainerHandler(proxy *Proxy, proxyURL string) *ContainerHandler {
 	return &ContainerHandler{
 		proxy:       proxy,
 		registryURL: dockerHubRegistry,
-		authURL:     dockerHubAuth,
 		proxyURL:    strings.TrimSuffix(proxyURL, "/"),
 	}
 }
@@ -89,31 +86,38 @@ func (h *ContainerHandler) handleBlobDownload(w http.ResponseWriter, r *http.Req
 
 	h.proxy.Logger.Info("container blob request", "name", name, "digest", digest)
 
-	// Get auth token for upstream
-	token, err := h.getAuthToken(r.Context(), name, "pull")
+	filename := digest
+	cached, err := h.proxy.GetCachedArtifact(r.Context(), "oci", name, digest, filename)
 	if err != nil {
-		h.proxy.Logger.Error("failed to get auth token", "error", err)
-		h.containerError(w, http.StatusUnauthorized, "UNAUTHORIZED", "failed to authenticate")
+		h.proxy.Logger.Error("failed to check blob cache", "error", err)
+		h.containerError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to check blob cache")
+		return
+	}
+	if cached != nil {
+		w.Header().Set("Docker-Content-Digest", digest)
+		w.Header().Set("Content-Type", "application/octet-stream")
+		if r.Method == http.MethodHead {
+			serveArtifactHead(w, cached)
+			return
+		}
+		ServeArtifact(w, cached)
 		return
 	}
 
 	// For HEAD requests, just proxy to upstream
 	if r.Method == http.MethodHead {
-		h.proxyBlobHead(w, r, name, digest, token)
+		h.proxyBlobHead(w, r, name, digest)
 		return
 	}
 
-	// Try to get from cache, or fetch from upstream with auth
-	filename := digest
-	headers := http.Header{"Authorization": {"Bearer " + token}}
-	result, err := h.proxy.GetOrFetchArtifactFromURLWithHeaders(
+	// Try to get from cache, or fetch from the authentication-aware upstream client.
+	result, err := h.proxy.GetOrFetchArtifactFromURL(
 		r.Context(),
 		"oci",
 		name,
 		digest, // use digest as version
 		filename,
 		fmt.Sprintf("%s/v2/%s/blobs/%s", h.registryURL, name, digest),
-		headers,
 	)
 
 	if err != nil {
@@ -127,8 +131,31 @@ func (h *ContainerHandler) handleBlobDownload(w http.ResponseWriter, r *http.Req
 	ServeArtifact(w, result)
 }
 
-// handleManifest proxies manifest requests to upstream.
-// Manifests change when tags are updated, so we proxy these directly.
+func serveArtifactHead(w http.ResponseWriter, result *CacheResult) {
+	if result.RedirectURL != "" {
+		if result.Hash != "" {
+			w.Header().Set("ETag", fmt.Sprintf(`"%s"`, result.Hash))
+		}
+		w.Header().Set("Location", result.RedirectURL)
+		w.WriteHeader(http.StatusFound)
+		return
+	}
+	if result.Reader != nil {
+		_ = result.Reader.Close()
+	}
+	if result.ContentType != "" {
+		w.Header().Set("Content-Type", result.ContentType)
+	}
+	if result.Size >= 0 {
+		w.Header().Set("Content-Length", fmt.Sprintf("%d", result.Size))
+	}
+	if result.Hash != "" {
+		w.Header().Set("ETag", fmt.Sprintf(`"%s"`, result.Hash))
+	}
+	w.WriteHeader(http.StatusOK)
+}
+
+// handleManifest serves immutable manifests from cache and revalidates mutable tags.
 // Path format: {name}/manifests/{reference}
 func (h *ContainerHandler) handleManifest(w http.ResponseWriter, r *http.Request, path string) {
 	if r.Method != http.MethodGet && r.Method != http.MethodHead {
@@ -143,57 +170,7 @@ func (h *ContainerHandler) handleManifest(w http.ResponseWriter, r *http.Request
 	}
 
 	h.proxy.Logger.Info("container manifest request", "name", name, "reference", reference)
-
-	// Get auth token
-	token, err := h.getAuthToken(r.Context(), name, "pull")
-	if err != nil {
-		h.proxy.Logger.Error("failed to get auth token", "error", err)
-		h.containerError(w, http.StatusUnauthorized, "UNAUTHORIZED", "failed to authenticate")
-		return
-	}
-
-	// Proxy to upstream
-	upstreamURL := fmt.Sprintf("%s/v2/%s/manifests/%s", h.registryURL, name, reference)
-
-	req, err := http.NewRequestWithContext(r.Context(), r.Method, upstreamURL, nil)
-	if err != nil {
-		h.containerError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to create request")
-		return
-	}
-
-	req.Header.Set("Authorization", "Bearer "+token)
-
-	// Forward Accept header for content negotiation
-	if accept := r.Header.Get("Accept"); accept != "" {
-		req.Header.Set("Accept", accept)
-	} else {
-		// Default accept headers for manifests
-		req.Header.Set("Accept", strings.Join([]string{
-			"application/vnd.oci.image.manifest.v1+json",
-			"application/vnd.oci.image.index.v1+json",
-			"application/vnd.docker.distribution.manifest.v2+json",
-			"application/vnd.docker.distribution.manifest.list.v2+json",
-			"application/vnd.docker.distribution.manifest.v1+prettyjws",
-		}, ", "))
-	}
-
-	resp, err := h.proxy.HTTPClient.Do(req)
-	if err != nil {
-		h.proxy.Logger.Error("failed to fetch manifest", "error", err)
-		h.containerError(w, http.StatusBadGateway, "INTERNAL_ERROR", "failed to fetch from upstream")
-		return
-	}
-	defer func() { _ = resp.Body.Close() }()
-
-	// Copy relevant headers
-	for _, header := range []string{"Content-Type", "Content-Length", "Docker-Content-Digest", "ETag"} {
-		if v := resp.Header.Get(header); v != "" {
-			w.Header().Set(header, v)
-		}
-	}
-
-	w.WriteHeader(resp.StatusCode)
-	_, _ = io.Copy(w, resp.Body)
+	h.serveManifest(w, r, name, reference)
 }
 
 // handleTagsList proxies tag list requests to upstream.
@@ -209,13 +186,6 @@ func (h *ContainerHandler) handleTagsList(w http.ResponseWriter, r *http.Request
 		return
 	}
 
-	// Get auth token
-	token, err := h.getAuthToken(r.Context(), name, "pull")
-	if err != nil {
-		h.containerError(w, http.StatusUnauthorized, "UNAUTHORIZED", "failed to authenticate")
-		return
-	}
-
 	upstreamURL := fmt.Sprintf("%s/v2/%s/tags/list", h.registryURL, name)
 	if r.URL.RawQuery != "" {
 		upstreamURL += "?" + r.URL.RawQuery
@@ -227,8 +197,6 @@ func (h *ContainerHandler) handleTagsList(w http.ResponseWriter, r *http.Request
 		return
 	}
 
-	req.Header.Set("Authorization", "Bearer "+token)
-
 	resp, err := h.proxy.HTTPClient.Do(req)
 	if err != nil {
 		h.containerError(w, http.StatusBadGateway, "INTERNAL_ERROR", "failed to fetch from upstream")
@@ -241,45 +209,8 @@ func (h *ContainerHandler) handleTagsList(w http.ResponseWriter, r *http.Request
 	_, _ = io.Copy(w, resp.Body)
 }
 
-// getAuthToken gets a bearer token for the specified repository.
-// Docker Hub requires auth even for public images.
-func (h *ContainerHandler) getAuthToken(_ interface{ Done() <-chan struct{} }, repository, action string) (string, error) {
-	// For Docker Hub: https://auth.docker.io/token?service=registry.docker.io&scope=repository:{repo}:pull
-	authURL := fmt.Sprintf("%s/token?service=registry.docker.io&scope=repository:%s:%s",
-		h.authURL, repository, action)
-
-	req, err := http.NewRequest(http.MethodGet, authURL, nil)
-	if err != nil {
-		return "", err
-	}
-
-	resp, err := h.proxy.HTTPClient.Do(req)
-	if err != nil {
-		return "", err
-	}
-	defer func() { _ = resp.Body.Close() }()
-
-	if resp.StatusCode != http.StatusOK {
-		return "", fmt.Errorf("auth failed with status %d", resp.StatusCode)
-	}
-
-	var tokenResp struct {
-		Token       string `json:"token"`
-		AccessToken string `json:"access_token"`
-	}
-
-	if err := json.NewDecoder(resp.Body).Decode(&tokenResp); err != nil {
-		return "", err
-	}
-
-	if tokenResp.Token != "" {
-		return tokenResp.Token, nil
-	}
-	return tokenResp.AccessToken, nil
-}
-
 // proxyBlobHead handles HEAD requests for blobs.
-func (h *ContainerHandler) proxyBlobHead(w http.ResponseWriter, r *http.Request, name, digest, token string) {
+func (h *ContainerHandler) proxyBlobHead(w http.ResponseWriter, r *http.Request, name, digest string) {
 	upstreamURL := fmt.Sprintf("%s/v2/%s/blobs/%s", h.registryURL, name, digest)
 
 	req, err := http.NewRequestWithContext(r.Context(), http.MethodHead, upstreamURL, nil)
@@ -288,8 +219,6 @@ func (h *ContainerHandler) proxyBlobHead(w http.ResponseWriter, r *http.Request,
 		return
 	}
 
-	req.Header.Set("Authorization", "Bearer "+token)
-
 	resp, err := h.proxy.HTTPClient.Do(req)
 	if err != nil {
 		h.containerError(w, http.StatusBadGateway, "INTERNAL_ERROR", "failed to fetch from upstream")

internal/handler/container_manifest.go

@@ -0,0 +1,251 @@
+package handler
+
+import (
+	"bytes"
+	"context"
+	"crypto/sha256"
+	"database/sql"
+	"encoding/hex"
+	"fmt"
+	"io"
+	"net/http"
+	"regexp"
+	"strconv"
+	"strings"
+	"time"
+
+	"github.com/git-pkgs/proxy/internal/database"
+)
+
+const (
+	containerManifestCacheEcosystem = "oci-manifest"
+	containerStaleWarning           = `110 - "Response is Stale"`
+)
+
+var manifestDigestReferencePattern = regexp.MustCompile(`^[a-z0-9]+:[a-f0-9]+$`)
+
+type cachedContainerManifest struct {
+	body          []byte
+	contentType   string
+	contentDigest string
+	etag          string
+	size          int64
+	fetchedAt     time.Time
+}
+
+func (h *ContainerHandler) serveManifest(w http.ResponseWriter, r *http.Request, name, reference string) {
+	accept := containerManifestAccept(r)
+	cacheKey := h.containerManifestCacheKey(name, reference, accept)
+	cached, err := h.loadContainerManifest(r.Context(), cacheKey)
+	if err != nil {
+		h.proxy.Logger.Warn("failed to read cached container manifest", "error", err)
+		cached = nil
+	}
+
+	immutable := manifestDigestReferencePattern.MatchString(reference)
+	if cached != nil && (immutable || h.containerManifestFresh(cached)) {
+		writeContainerManifest(w, r.Method, cached, false)
+		return
+	}
+
+	upstreamURL := fmt.Sprintf("%s/v2/%s/manifests/%s", h.registryURL, name, reference)
+	req, err := http.NewRequestWithContext(r.Context(), r.Method, upstreamURL, nil)
+	if err != nil {
+		h.containerError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to create request")
+		return
+	}
+	req.Header.Set("Accept", accept)
+	if cached != nil && cached.etag != "" {
+		req.Header.Set("If-None-Match", cached.etag)
+	}
+
+	resp, err := h.proxy.HTTPClient.Do(req)
+	if err != nil {
+		h.serveStaleManifestOrError(w, r, cached, err)
+		return
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	if resp.StatusCode == http.StatusNotModified && cached != nil {
+		cached.fetchedAt = time.Now()
+		if err := h.storeContainerManifest(r.Context(), cacheKey, cached); err != nil {
+			h.proxy.Logger.Warn("failed to refresh cached container manifest", "error", err)
+		}
+		writeContainerManifest(w, r.Method, cached, false)
+		return
+	}
+	if resp.StatusCode != http.StatusOK {
+		if cached != nil && shouldServeStaleManifest(resp.StatusCode) {
+			writeContainerManifest(w, r.Method, cached, true)
+			return
+		}
+		copyContainerManifestHeaders(w.Header(), resp.Header)
+		w.WriteHeader(resp.StatusCode)
+		_, _ = io.Copy(w, resp.Body)
+		return
+	}
+
+	if r.Method == http.MethodHead {
+		copyContainerManifestHeaders(w.Header(), resp.Header)
+		w.WriteHeader(http.StatusOK)
+		return
+	}
+
+	body, err := h.proxy.ReadMetadata(resp.Body)
+	if err != nil {
+		h.serveStaleManifestOrError(w, r, cached, fmt.Errorf("reading manifest: %w", err))
+		return
+	}
+	manifest := &cachedContainerManifest{
+		body:          body,
+		contentType:   resp.Header.Get("Content-Type"),
+		contentDigest: resp.Header.Get("Docker-Content-Digest"),
+		etag:          resp.Header.Get("ETag"),
+		size:          int64(len(body)),
+		fetchedAt:     time.Now(),
+	}
+	if manifest.contentDigest == "" {
+		manifest.contentDigest = sha256Digest(body)
+	}
+	if err := h.storeContainerManifest(r.Context(), cacheKey, manifest); err != nil {
+		h.proxy.Logger.Warn("failed to cache container manifest", "error", err)
+	}
+	if manifest.contentDigest != reference && manifestDigestReferencePattern.MatchString(manifest.contentDigest) {
+		digestKey := h.containerManifestCacheKey(name, manifest.contentDigest, accept)
+		if err := h.storeContainerManifest(r.Context(), digestKey, manifest); err != nil {
+			h.proxy.Logger.Warn("failed to cache container manifest by digest", "error", err)
+		}
+	}
+	writeContainerManifest(w, r.Method, manifest, false)
+}
+
+func (h *ContainerHandler) serveStaleManifestOrError(w http.ResponseWriter, r *http.Request, cached *cachedContainerManifest, err error) {
+	if cached != nil {
+		h.proxy.Logger.Warn("upstream manifest fetch failed, serving stale cache", "error", err)
+		writeContainerManifest(w, r.Method, cached, true)
+		return
+	}
+	h.proxy.Logger.Error("failed to fetch manifest", "error", err)
+	h.containerError(w, http.StatusBadGateway, "INTERNAL_ERROR", "failed to fetch from upstream")
+}
+
+func (h *ContainerHandler) containerManifestFresh(manifest *cachedContainerManifest) bool {
+	return h.proxy.MetadataTTL > 0 && !manifest.fetchedAt.IsZero() && time.Since(manifest.fetchedAt) < h.proxy.MetadataTTL
+}
+
+func (h *ContainerHandler) containerManifestCacheKey(name, reference, accept string) string {
+	identity := strings.Join([]string{h.registryURL, name, reference, accept}, "\x00")
+	sum := sha256.Sum256([]byte(identity))
+	return hex.EncodeToString(sum[:])
+}
+
+func (h *ContainerHandler) loadContainerManifest(ctx context.Context, cacheKey string) (*cachedContainerManifest, error) {
+	if h.proxy.DB == nil || h.proxy.Storage == nil {
+		return nil, nil
+	}
+	entry, err := h.proxy.DB.GetMetadataCache(containerManifestCacheEcosystem, cacheKey)
+	if err != nil || entry == nil {
+		return nil, err
+	}
+	reader, err := h.proxy.Storage.Open(ctx, entry.StoragePath)
+	if err != nil {
+		return nil, nil
+	}
+	defer func() { _ = reader.Close() }()
+	body, err := h.proxy.ReadMetadata(reader)
+	if err != nil {
+		return nil, err
+	}
+
+	manifest := &cachedContainerManifest{body: body, size: int64(len(body))}
+	if entry.ContentType.Valid {
+		manifest.contentType = entry.ContentType.String
+	}
+	if entry.ContentDigest.Valid {
+		manifest.contentDigest = entry.ContentDigest.String
+	} else {
+		manifest.contentDigest = sha256Digest(body)
+	}
+	if entry.ETag.Valid {
+		manifest.etag = entry.ETag.String
+	}
+	if entry.Size.Valid {
+		manifest.size = entry.Size.Int64
+	}
+	if entry.FetchedAt.Valid {
+		manifest.fetchedAt = entry.FetchedAt.Time
+	}
+	return manifest, nil
+}
+
+func (h *ContainerHandler) storeContainerManifest(ctx context.Context, cacheKey string, manifest *cachedContainerManifest) error {
+	if h.proxy.DB == nil || h.proxy.Storage == nil {
+		return nil
+	}
+	storagePath := metadataStoragePath(containerManifestCacheEcosystem, cacheKey)
+	size, _, err := h.proxy.Storage.Store(ctx, storagePath, bytes.NewReader(manifest.body))
+	if err != nil {
+		return fmt.Errorf("storing manifest: %w", err)
+	}
+	manifest.size = size
+	return h.proxy.DB.UpsertMetadataCache(&database.MetadataCacheEntry{
+		Ecosystem:     containerManifestCacheEcosystem,
+		Name:          cacheKey,
+		StoragePath:   storagePath,
+		ETag:          sql.NullString{String: manifest.etag, Valid: manifest.etag != ""},
+		ContentType:   sql.NullString{String: manifest.contentType, Valid: manifest.contentType != ""},
+		ContentDigest: sql.NullString{String: manifest.contentDigest, Valid: manifest.contentDigest != ""},
+		Size:          sql.NullInt64{Int64: size, Valid: true},
+		FetchedAt:     sql.NullTime{Time: manifest.fetchedAt, Valid: !manifest.fetchedAt.IsZero()},
+	})
+}
+
+func writeContainerManifest(w http.ResponseWriter, method string, manifest *cachedContainerManifest, stale bool) {
+	if manifest.contentType != "" {
+		w.Header().Set("Content-Type", manifest.contentType)
+	}
+	w.Header().Set("Content-Length", strconv.FormatInt(manifest.size, 10))
+	if manifest.contentDigest != "" {
+		w.Header().Set("Docker-Content-Digest", manifest.contentDigest)
+	}
+	if manifest.etag != "" {
+		w.Header().Set("ETag", manifest.etag)
+	}
+	if stale {
+		w.Header().Set("Warning", containerStaleWarning)
+	}
+	w.WriteHeader(http.StatusOK)
+	if method != http.MethodHead {
+		_, _ = w.Write(manifest.body)
+	}
+}
+
+func containerManifestAccept(r *http.Request) string {
+	if accept := r.Header.Get("Accept"); accept != "" {
+		return accept
+	}
+	return strings.Join([]string{
+		"application/vnd.oci.image.manifest.v1+json",
+		"application/vnd.oci.image.index.v1+json",
+		"application/vnd.docker.distribution.manifest.v2+json",
+		"application/vnd.docker.distribution.manifest.list.v2+json",
+		"application/vnd.docker.distribution.manifest.v1+prettyjws",
+	}, ", ")
+}
+
+func copyContainerManifestHeaders(destination, source http.Header) {
+	for _, header := range []string{"Content-Type", "Content-Length", "Docker-Content-Digest", "ETag", "WWW-Authenticate"} {
+		if value := source.Get(header); value != "" {
+			destination.Set(header, value)
+		}
+	}
+}
+
+func shouldServeStaleManifest(status int) bool {
+	return status == http.StatusTooManyRequests || status >= http.StatusInternalServerError
+}
+
+func sha256Digest(body []byte) string {
+	digest := sha256.Sum256(body)
+	return "sha256:" + hex.EncodeToString(digest[:])
+}

internal/handler/container_test.go

@@ -1,16 +1,14 @@
 package handler
 
 import (
-	"bytes"
-	"context"
 	"encoding/json"
 	"io"
-	"log/slog"
 	"net/http"
 	"net/http/httptest"
+	"strconv"
 	"testing"
 
-	"github.com/git-pkgs/proxy/internal/database"
+	upstreamhttp "github.com/git-pkgs/proxy/internal/httpclient"
 	"github.com/git-pkgs/registries/fetch"
 )
 
@@ -135,90 +133,387 @@ func TestContainerHandler_parseTagsListPath(t *testing.T) {
 	}
 }
 
-func TestContainerHandler_BlobDownload_CachesWithAuth(t *testing.T) {
-	// Set up a mock auth server that returns a token
-	authServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+func TestContainerHandler_BlobDownload_DiscoversBearerChallenge(t *testing.T) {
+	digest := "sha256:abc123def456abc123def456abc123def456abc123def456abc123def456abcd"
+	registryRequests := 0
+	tokenRequests := 0
+	var upstream *httptest.Server
+	upstream = httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		switch r.URL.Path {
+		case "/token":
+			tokenRequests++
 			w.Header().Set("Content-Type", "application/json")
-		_ = json.NewEncoder(w).Encode(map[string]string{"token": "test-token-123"})
+			_ = json.NewEncoder(w).Encode(map[string]any{
+				"token":      "discovered-token",
+				"expires_in": 3600,
+			})
+		case "/v2/library/nginx/blobs/" + digest:
+			registryRequests++
+			if r.Header.Get("Authorization") != "Bearer discovered-token" {
+				w.Header().Set("WWW-Authenticate", `Bearer realm="`+upstream.URL+`/token",service="registry.test",scope="repository:library/nginx:pull"`)
+				http.Error(w, "authentication required", http.StatusUnauthorized)
+				return
+			}
+			w.Header().Set("Content-Type", "application/octet-stream")
+			_, _ = io.WriteString(w, "upstream blob")
+		default:
+			http.NotFound(w, r)
+		}
 	}))
-	defer authServer.Close()
+	defer upstream.Close()
 
-	// Set up mock fetcher that captures headers
-	var capturedHeaders http.Header
-	mf := &mockFetcherWithHeaders{
-		fetchFn: func(_ context.Context, _ string, headers http.Header) (*fetch.Artifact, error) {
-			capturedHeaders = headers
-			return &fetch.Artifact{
-				Body:        io.NopCloser(bytes.NewReader([]byte("blob-content"))),
-				Size:        12,
-				ContentType: "application/octet-stream",
-			}, nil
-		},
-	}
-
-	dir := t.TempDir()
-	db, err := database.Create(dir + "/test.db")
-	if err != nil {
-		t.Fatalf("failed to create test database: %v", err)
-	}
-	t.Cleanup(func() { _ = db.Close() })
-
-	store := newMockStorage()
-	logger := slog.New(slog.NewTextHandler(io.Discard, nil))
-	proxy := &Proxy{
-		DB:         db,
-		Storage:    store,
-		Fetcher:    mf,
-		Logger:     logger,
-		HTTPClient: &http.Client{},
-	}
+	proxy, _, _, _ := setupTestProxy(t)
+	authTransport := upstreamhttp.NewTransport(http.DefaultTransport, nil)
+	client := &http.Client{Transport: authTransport}
+	artifactFetcher := fetch.NewFetcher(
+		fetch.WithHTTPClient(client),
+		fetch.WithMaxRetries(0),
+	)
+	t.Cleanup(func() { _ = artifactFetcher.Close() })
+	proxy.Fetcher = artifactFetcher
+	proxy.HTTPClient = client
 
 	h := &ContainerHandler{
 		proxy:       proxy,
-		registryURL: "https://registry-1.docker.io",
-		authURL:     authServer.URL,
+		registryURL: upstream.URL,
 		proxyURL:    "http://localhost:8080",
 	}
 
-	handler := h.Routes()
-	req := httptest.NewRequest(http.MethodGet, "/library/nginx/blobs/sha256:abc123def456abc123def456abc123def456abc123def456abc123def456abcd", nil)
+	for range 2 {
+		req := httptest.NewRequest(http.MethodGet, "/library/nginx/blobs/"+digest, nil)
 		w := httptest.NewRecorder()
-	handler.ServeHTTP(w, req)
+		h.Routes().ServeHTTP(w, req)
+		if w.Code != http.StatusOK {
+			t.Fatalf("status = %d, want %d; body: %s", w.Code, http.StatusOK, w.Body.String())
+		}
+		if got := w.Body.String(); got != "upstream blob" {
+			t.Errorf("body = %q, want %q", got, "upstream blob")
+		}
+	}
+
+	if tokenRequests != 1 {
+		t.Errorf("token requests = %d, want 1", tokenRequests)
+	}
+	if registryRequests != 2 {
+		t.Errorf("registry requests = %d, want 2", registryRequests)
+	}
+}
+
+func TestContainerHandler_BlobDownload_CacheHitSkipsAuth(t *testing.T) {
+	proxy, db, store, fetcher := setupTestProxy(t)
+	digest := "sha256:abc123def456abc123def456abc123def456abc123def456abc123def456abcd"
+	seedPackage(t, db, store, "oci", "library/nginx", digest, digest, "cached blob")
+
+	upstreamRequests := 0
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		upstreamRequests++
+		http.Error(w, "upstream unavailable", http.StatusServiceUnavailable)
+	}))
+	defer upstream.Close()
+
+	h := &ContainerHandler{
+		proxy:       proxy,
+		registryURL: upstream.URL,
+		proxyURL:    "http://localhost:8080",
+	}
+
+	req := httptest.NewRequest(http.MethodGet, "/library/nginx/blobs/"+digest, nil)
+	w := httptest.NewRecorder()
+	h.Routes().ServeHTTP(w, req)
 
 	if w.Code != http.StatusOK {
-		t.Errorf("got status %d, want %d; body: %s", w.Code, http.StatusOK, w.Body.String())
+		t.Fatalf("status = %d, want %d; body: %s", w.Code, http.StatusOK, w.Body.String())
 	}
-
-	// Verify auth header was passed to the fetcher
-	if capturedHeaders == nil {
-		t.Fatal("expected headers to be passed to fetcher, got nil")
+	if got := w.Body.String(); got != "cached blob" {
+		t.Errorf("body = %q, want %q", got, "cached blob")
 	}
-	auth := capturedHeaders.Get("Authorization")
-	if auth != "Bearer test-token-123" {
-		t.Errorf("Authorization = %q, want %q", auth, "Bearer test-token-123")
+	if upstreamRequests != 0 {
+		t.Errorf("upstream requests = %d, want 0", upstreamRequests)
 	}
-
-	// Verify response headers
-	if got := w.Header().Get("Docker-Content-Digest"); got != "sha256:abc123def456abc123def456abc123def456abc123def456abc123def456abcd" {
-		t.Errorf("Docker-Content-Digest = %q, want digest", got)
+	if fetcher.fetchCalled {
+		t.Error("fetcher should not be called on cache hit")
 	}
 }
 
-// mockFetcherWithHeaders captures headers passed to FetchWithHeaders.
-type mockFetcherWithHeaders struct {
-	fetchFn func(ctx context.Context, url string, headers http.Header) (*fetch.Artifact, error)
+func TestContainerHandler_BlobHead_CacheHitSkipsUpstreamAndAuth(t *testing.T) {
+	proxy, db, store, fetcher := setupTestProxy(t)
+	digest := "sha256:abc123def456abc123def456abc123def456abc123def456abc123def456abcd"
+	seedPackage(t, db, store, "oci", "library/nginx", digest, digest, "cached blob")
+
+	upstreamRequests := 0
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		upstreamRequests++
+		http.Error(w, "upstream unavailable", http.StatusServiceUnavailable)
+	}))
+	defer upstream.Close()
+	proxy.HTTPClient = upstream.Client()
+
+	h := &ContainerHandler{
+		proxy:       proxy,
+		registryURL: upstream.URL,
+		proxyURL:    "http://localhost:8080",
+	}
+
+	req := httptest.NewRequest(http.MethodHead, "/library/nginx/blobs/"+digest, nil)
+	w := httptest.NewRecorder()
+	h.Routes().ServeHTTP(w, req)
+
+	if w.Code != http.StatusOK {
+		t.Fatalf("status = %d, want %d; body: %s", w.Code, http.StatusOK, w.Body.String())
+	}
+	if got := w.Header().Get("Docker-Content-Digest"); got != digest {
+		t.Errorf("Docker-Content-Digest = %q, want %q", got, digest)
+	}
+	if got := w.Header().Get("Content-Length"); got != "11" {
+		t.Errorf("Content-Length = %q, want %q", got, "11")
+	}
+	if w.Body.Len() != 0 {
+		t.Errorf("HEAD response body length = %d, want 0", w.Body.Len())
+	}
+	if upstreamRequests != 0 {
+		t.Errorf("upstream requests = %d, want 0", upstreamRequests)
+	}
+	if fetcher.fetchCalled {
+		t.Error("fetcher should not be called on cache hit")
+	}
 }
 
-func (f *mockFetcherWithHeaders) Fetch(ctx context.Context, url string) (*fetch.Artifact, error) {
-	return f.FetchWithHeaders(ctx, url, nil)
+func TestContainerHandler_BlobHead_DirectServeRedirects(t *testing.T) {
+	proxy, db, store, fetcher := setupTestProxy(t)
+	digest := "sha256:abc123def456abc123def456abc123def456abc123def456abc123def456abcd"
+	seedPackage(t, db, store, "oci", "library/nginx", digest, digest, "cached blob")
+	store.signedURL = "https://storage.example.test/cached-blob?signature=test"
+	proxy.DirectServe = true
+
+	h := &ContainerHandler{
+		proxy:       proxy,
+		registryURL: "https://registry.example.test",
+		proxyURL:    "http://localhost:8080",
+	}
+
+	req := httptest.NewRequest(http.MethodHead, "/library/nginx/blobs/"+digest, nil)
+	w := httptest.NewRecorder()
+	h.Routes().ServeHTTP(w, req)
+
+	if w.Code != http.StatusFound {
+		t.Fatalf("status = %d, want %d", w.Code, http.StatusFound)
+	}
+	if got := w.Header().Get("Location"); got != store.signedURL {
+		t.Errorf("Location = %q, want %q", got, store.signedURL)
+	}
+	if got := w.Header().Get("ETag"); got != `"abc123"` {
+		t.Errorf("ETag = %q, want %q", got, `"abc123"`)
+	}
+	if w.Body.Len() != 0 {
+		t.Errorf("HEAD response body length = %d, want 0", w.Body.Len())
+	}
+	if fetcher.fetchCalled {
+		t.Error("fetcher should not be called on cache hit")
+	}
 }
 
-func (f *mockFetcherWithHeaders) FetchWithHeaders(ctx context.Context, url string, headers http.Header) (*fetch.Artifact, error) {
-	return f.fetchFn(ctx, url, headers)
+func TestContainerHandler_ManifestByDigest_CacheHitSkipsUpstream(t *testing.T) {
+	digest := "sha256:aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa"
+	manifest := `{"schemaVersion":2,"mediaType":"application/vnd.oci.image.manifest.v1+json"}`
+	upstreamAvailable := true
+	upstreamRequests := 0
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		upstreamRequests++
+		if !upstreamAvailable {
+			http.Error(w, "upstream unavailable", http.StatusServiceUnavailable)
+			return
+		}
+		if r.URL.Path != "/v2/library/nginx/manifests/"+digest {
+			http.NotFound(w, r)
+			return
+		}
+		w.Header().Set("Content-Type", "application/vnd.oci.image.manifest.v1+json")
+		w.Header().Set("Docker-Content-Digest", digest)
+		w.Header().Set("ETag", `"manifest-etag"`)
+		if r.Method != http.MethodHead {
+			_, _ = io.WriteString(w, manifest)
+		}
+	}))
+	defer upstream.Close()
+
+	proxy, _, _, _ := setupTestProxy(t)
+	proxy.HTTPClient = upstream.Client()
+	h := &ContainerHandler{proxy: proxy, registryURL: upstream.URL, proxyURL: "http://localhost:8080"}
+
+	first := httptest.NewRecorder()
+	h.Routes().ServeHTTP(first, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/"+digest, nil))
+	if first.Code != http.StatusOK {
+		t.Fatalf("initial status = %d, want %d; body: %s", first.Code, http.StatusOK, first.Body.String())
+	}
+	if first.Body.String() != manifest {
+		t.Fatalf("initial body = %q, want %q", first.Body.String(), manifest)
+	}
+
+	upstreamAvailable = false
+	second := httptest.NewRecorder()
+	h.Routes().ServeHTTP(second, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/"+digest, nil))
+	if second.Code != http.StatusOK {
+		t.Fatalf("cached status = %d, want %d; body: %s", second.Code, http.StatusOK, second.Body.String())
+	}
+	if second.Body.String() != manifest {
+		t.Errorf("cached body = %q, want %q", second.Body.String(), manifest)
+	}
+	if got := second.Header().Get("Docker-Content-Digest"); got != digest {
+		t.Errorf("cached Docker-Content-Digest = %q, want %q", got, digest)
+	}
+
+	head := httptest.NewRecorder()
+	h.Routes().ServeHTTP(head, httptest.NewRequest(http.MethodHead, "/library/nginx/manifests/"+digest, nil))
+	if head.Code != http.StatusOK {
+		t.Fatalf("cached HEAD status = %d, want %d", head.Code, http.StatusOK)
+	}
+	wantLength := strconv.Itoa(len(manifest))
+	if got := head.Header().Get("Content-Length"); got != wantLength {
+		t.Errorf("cached HEAD Content-Length = %q, want %q", got, wantLength)
+	}
+	if head.Body.Len() != 0 {
+		t.Errorf("cached HEAD body length = %d, want 0", head.Body.Len())
+	}
+	if upstreamRequests != 1 {
+		t.Errorf("upstream requests = %d, want 1", upstreamRequests)
+	}
 }
 
-func (f *mockFetcherWithHeaders) Head(_ context.Context, _ string) (int64, string, error) {
-	return 0, "", nil
+func TestContainerHandler_ManifestByTag_UsesStaleCacheOnUpstreamFailure(t *testing.T) {
+	digest := "sha256:bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb"
+	manifest := `{"schemaVersion":2,"mediaType":"application/vnd.oci.image.index.v1+json"}`
+	upstreamAvailable := true
+	upstreamRequests := 0
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		upstreamRequests++
+		if !upstreamAvailable {
+			http.Error(w, "upstream unavailable", http.StatusServiceUnavailable)
+			return
+		}
+		w.Header().Set("Content-Type", "application/vnd.oci.image.index.v1+json")
+		w.Header().Set("Docker-Content-Digest", digest)
+		_, _ = io.WriteString(w, manifest)
+	}))
+	defer upstream.Close()
+
+	proxy, _, _, _ := setupTestProxy(t)
+	proxy.HTTPClient = upstream.Client()
+	proxy.MetadataTTL = 0
+	h := &ContainerHandler{proxy: proxy, registryURL: upstream.URL, proxyURL: "http://localhost:8080"}
+
+	first := httptest.NewRecorder()
+	h.Routes().ServeHTTP(first, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/latest", nil))
+	if first.Code != http.StatusOK {
+		t.Fatalf("initial status = %d, want %d; body: %s", first.Code, http.StatusOK, first.Body.String())
+	}
+
+	upstreamAvailable = false
+	second := httptest.NewRecorder()
+	h.Routes().ServeHTTP(second, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/latest", nil))
+	if second.Code != http.StatusOK {
+		t.Fatalf("stale status = %d, want %d; body: %s", second.Code, http.StatusOK, second.Body.String())
+	}
+	if second.Body.String() != manifest {
+		t.Errorf("stale body = %q, want %q", second.Body.String(), manifest)
+	}
+	if got := second.Header().Get("Warning"); got != `110 - "Response is Stale"` {
+		t.Errorf("Warning = %q, want stale warning", got)
+	}
+	if got := second.Header().Get("Docker-Content-Digest"); got != digest {
+		t.Errorf("stale Docker-Content-Digest = %q, want %q", got, digest)
+	}
+	if upstreamRequests != 2 {
+		t.Errorf("upstream requests = %d, want 2", upstreamRequests)
+	}
+}
+
+func TestContainerHandler_ManifestByTag_CachesDigestAlias(t *testing.T) {
+	digest := "sha256:cccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccc"
+	manifest := `{"schemaVersion":2,"mediaType":"application/vnd.oci.image.manifest.v1+json"}`
+	upstreamAvailable := true
+	upstreamRequests := 0
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		upstreamRequests++
+		if !upstreamAvailable {
+			http.Error(w, "upstream unavailable", http.StatusServiceUnavailable)
+			return
+		}
+		if r.URL.Path != "/v2/library/nginx/manifests/latest" {
+			http.NotFound(w, r)
+			return
+		}
+		w.Header().Set("Content-Type", "application/vnd.oci.image.manifest.v1+json")
+		w.Header().Set("Docker-Content-Digest", digest)
+		_, _ = io.WriteString(w, manifest)
+	}))
+	defer upstream.Close()
+
+	proxy, _, _, _ := setupTestProxy(t)
+	proxy.HTTPClient = upstream.Client()
+	h := &ContainerHandler{proxy: proxy, registryURL: upstream.URL, proxyURL: "http://localhost:8080"}
+
+	first := httptest.NewRecorder()
+	h.Routes().ServeHTTP(first, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/latest", nil))
+	if first.Code != http.StatusOK {
+		t.Fatalf("tag status = %d, want %d; body: %s", first.Code, http.StatusOK, first.Body.String())
+	}
+
+	upstreamAvailable = false
+	byDigest := httptest.NewRecorder()
+	h.Routes().ServeHTTP(byDigest, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/"+digest, nil))
+	if byDigest.Code != http.StatusOK {
+		t.Fatalf("digest status = %d, want %d; body: %s", byDigest.Code, http.StatusOK, byDigest.Body.String())
+	}
+	if byDigest.Body.String() != manifest {
+		t.Errorf("digest body = %q, want %q", byDigest.Body.String(), manifest)
+	}
+	if got := byDigest.Header().Get("Docker-Content-Digest"); got != digest {
+		t.Errorf("Docker-Content-Digest = %q, want %q", got, digest)
+	}
+	if upstreamRequests != 1 {
+		t.Errorf("upstream requests = %d, want 1", upstreamRequests)
+	}
+}
+
+func TestContainerHandler_ManifestByTag_StaleHeadChecksUpstream(t *testing.T) {
+	oldDigest := "sha256:dddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddd"
+	newDigest := "sha256:eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee"
+	currentDigest := oldDigest
+	upstreamRequests := 0
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		upstreamRequests++
+		w.Header().Set("Content-Type", "application/vnd.oci.image.manifest.v1+json")
+		w.Header().Set("Docker-Content-Digest", currentDigest)
+		w.Header().Set("ETag", `"`+currentDigest+`"`)
+		if r.Method != http.MethodHead {
+			_, _ = io.WriteString(w, `{"schemaVersion":2}`)
+		}
+	}))
+	defer upstream.Close()
+
+	proxy, _, _, _ := setupTestProxy(t)
+	proxy.HTTPClient = upstream.Client()
+	proxy.MetadataTTL = 0
+	h := &ContainerHandler{proxy: proxy, registryURL: upstream.URL, proxyURL: "http://localhost:8080"}
+
+	first := httptest.NewRecorder()
+	h.Routes().ServeHTTP(first, httptest.NewRequest(http.MethodGet, "/library/nginx/manifests/latest", nil))
+	if first.Code != http.StatusOK {
+		t.Fatalf("initial status = %d, want %d", first.Code, http.StatusOK)
+	}
+
+	currentDigest = newDigest
+	head := httptest.NewRecorder()
+	h.Routes().ServeHTTP(head, httptest.NewRequest(http.MethodHead, "/library/nginx/manifests/latest", nil))
+	if head.Code != http.StatusOK {
+		t.Fatalf("HEAD status = %d, want %d", head.Code, http.StatusOK)
+	}
+	if got := head.Header().Get("Docker-Content-Digest"); got != newDigest {
+		t.Errorf("Docker-Content-Digest = %q, want %q", got, newDigest)
+	}
+	if upstreamRequests != 2 {
+		t.Errorf("upstream requests = %d, want 2", upstreamRequests)
+	}
 }
 
 func TestContainerHandler_Routes_VersionCheck(t *testing.T) {

internal/handler/handler.go

@@ -127,18 +127,25 @@ type CacheResult struct {
 
 // GetOrFetchArtifact retrieves an artifact from cache or fetches from upstream.
 func (p *Proxy) GetOrFetchArtifact(ctx context.Context, ecosystem, name, version, filename string) (*CacheResult, error) {
-	pkgPURL := purl.MakePURLString(ecosystem, name, "")
-	versionPURL := purl.MakePURLString(ecosystem, name, version)
-
-	if cached, err := p.checkCache(ctx, pkgPURL, versionPURL, filename); err != nil {
+	if cached, err := p.GetCachedArtifact(ctx, ecosystem, name, version, filename); err != nil {
 		return nil, err
 	} else if cached != nil {
 		return cached, nil
 	}
 
+	pkgPURL := purl.MakePURLString(ecosystem, name, "")
+	versionPURL := purl.MakePURLString(ecosystem, name, version)
 	return p.fetchAndCache(ctx, ecosystem, name, version, filename, pkgPURL, versionPURL)
 }
 
+// GetCachedArtifact retrieves an artifact from cache without contacting an upstream.
+// It returns nil when no usable cache entry exists.
+func (p *Proxy) GetCachedArtifact(ctx context.Context, ecosystem, name, version, filename string) (*CacheResult, error) {
+	pkgPURL := purl.MakePURLString(ecosystem, name, "")
+	versionPURL := purl.MakePURLString(ecosystem, name, version)
+	return p.checkCache(ctx, pkgPURL, versionPURL, filename)
+}
+
 // checkCache looks up an artifact in the cache. Returns nil if not cached.
 func (p *Proxy) checkCache(ctx context.Context, pkgPURL, versionPURL, filename string) (*CacheResult, error) {
 	pkg, err := p.DB.GetPackageByPURL(pkgPURL)
@@ -766,18 +773,16 @@ func (p *Proxy) GetOrFetchArtifactFromURL(ctx context.Context, ecosystem, name,
 }
 
 // GetOrFetchArtifactFromURLWithHeaders retrieves an artifact from cache or fetches from a URL
-// with additional HTTP headers. This is needed for registries that require authentication
-// (e.g. Docker Hub requires a Bearer token even for public images).
+// with additional request-specific HTTP headers.
 func (p *Proxy) GetOrFetchArtifactFromURLWithHeaders(ctx context.Context, ecosystem, name, version, filename, downloadURL string, headers http.Header) (*CacheResult, error) {
-	pkgPURL := purl.MakePURLString(ecosystem, name, "")
-	versionPURL := purl.MakePURLString(ecosystem, name, version)
-
-	if cached, err := p.checkCache(ctx, pkgPURL, versionPURL, filename); err != nil {
+	if cached, err := p.GetCachedArtifact(ctx, ecosystem, name, version, filename); err != nil {
 		return nil, err
 	} else if cached != nil {
 		return cached, nil
 	}
 
+	pkgPURL := purl.MakePURLString(ecosystem, name, "")
+	versionPURL := purl.MakePURLString(ecosystem, name, version)
 	return p.fetchAndCacheFromURL(ctx, ecosystem, name, version, filename, pkgPURL, versionPURL, downloadURL, headers)
 }
 

internal/handler/handler_test.go

@@ -5,7 +5,6 @@ import (
 	"context"
 	"database/sql"
 	"errors"
-	"fmt"
 	"io"
 	"log/slog"
 	"net/http"
@@ -16,6 +15,7 @@ import (
 
 	"github.com/git-pkgs/proxy/internal/database"
 	"github.com/git-pkgs/proxy/internal/storage"
+	"github.com/git-pkgs/purl"
 	"github.com/git-pkgs/registries/fetch"
 )
 
@@ -151,7 +151,7 @@ func seedPackage(t *testing.T, db *database.DB, store *mockStorage, ecosystem, n
 	t.Helper()
 
 	pkg := &database.Package{
-		PURL:      fmt.Sprintf("pkg:%s/%s", ecosystem, name),
+		PURL:      purl.MakePURLString(ecosystem, name, ""),
 		Ecosystem: ecosystem,
 		Name:      name,
 	}
@@ -159,7 +159,7 @@ func seedPackage(t *testing.T, db *database.DB, store *mockStorage, ecosystem, n
 		t.Fatalf("failed to upsert package: %v", err)
 	}
 
-	versionPURL := fmt.Sprintf("pkg:%s/%s@%s", ecosystem, name, version)
+	versionPURL := purl.MakePURLString(ecosystem, name, version)
 	ver := &database.Version{
 		PURL:        versionPURL,
 		PackagePURL: pkg.PURL,

internal/httpclient/transport.go

@@ -0,0 +1,418 @@
+// Package httpclient provides authentication-aware HTTP transports for upstream requests.
+package httpclient
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"io"
+	"net/http"
+	"net/url"
+	"strings"
+	"sync"
+	"time"
+)
+
+const (
+	defaultTokenLifetime  = 60 * time.Second
+	tokenExpirySkew       = 5 * time.Second
+	maxTokenResponseSize  = 1 << 20
+	shortTokenSkewDivisor = 10
+)
+
+// AuthFunc returns a configured authentication header for a URL.
+type AuthFunc func(url string) (headerName, headerValue string)
+
+// Transport adds configured authentication and follows OCI Bearer challenges.
+type Transport struct {
+	base       http.RoundTripper
+	authForURL AuthFunc
+
+	mu         sync.Mutex
+	tokens     map[string]cachedToken
+	challenges map[string]bearerChallenge
+}
+
+type cachedToken struct {
+	value     string
+	expiresAt time.Time
+}
+
+type bearerChallenge struct {
+	realm   string
+	service string
+	scopes  []string
+}
+
+type tokenResponse struct {
+	Token       string `json:"token"`
+	AccessToken string `json:"access_token"`
+	ExpiresIn   int64  `json:"expires_in"`
+	IssuedAt    string `json:"issued_at"`
+}
+
+// NewTransport creates an authentication-aware transport around base.
+func NewTransport(base http.RoundTripper, authForURL AuthFunc) *Transport {
+	if base == nil {
+		base = http.DefaultTransport
+	}
+	return &Transport{
+		base:       base,
+		authForURL: authForURL,
+		tokens:     make(map[string]cachedToken),
+		challenges: make(map[string]bearerChallenge),
+	}
+}
+
+// RoundTrip implements http.RoundTripper.
+func (t *Transport) RoundTrip(req *http.Request) (*http.Response, error) {
+	outbound := cloneRequest(req)
+	t.applyAuthentication(outbound, req.Header.Get("Authorization") != "")
+
+	resp, err := t.base.RoundTrip(outbound)
+	if err != nil || resp.StatusCode != http.StatusUnauthorized {
+		return resp, err
+	}
+	if registryProtectionSpace(req.URL) == "" {
+		return resp, nil
+	}
+
+	challenge, ok := parseBearerChallenge(resp.Header.Values("WWW-Authenticate"))
+	if !ok || !canReplay(req) {
+		return resp, nil
+	}
+
+	drainAndClose(resp.Body)
+	token, err := t.token(req.Context(), challenge)
+	if err != nil {
+		return nil, fmt.Errorf("registry authentication: %w", err)
+	}
+	t.rememberChallenge(req.URL, challenge)
+
+	retry, err := cloneRequestForRetry(req)
+	if err != nil {
+		return nil, err
+	}
+	t.applyConfiguredAuthentication(retry)
+	retry.Header.Set("Authorization", "Bearer "+token)
+	return t.base.RoundTrip(retry)
+}
+
+func (t *Transport) applyAuthentication(req *http.Request, hasExplicitAuthorization bool) {
+	t.applyConfiguredAuthentication(req)
+	if hasExplicitAuthorization {
+		return
+	}
+	if token := t.cachedTokenForRequest(req.URL); token != "" {
+		req.Header.Set("Authorization", "Bearer "+token)
+	}
+}
+
+func (t *Transport) applyConfiguredAuthentication(req *http.Request) {
+	if t.authForURL == nil {
+		return
+	}
+	name, value := t.authForURL(req.URL.String())
+	if name != "" && value != "" && req.Header.Get(name) == "" {
+		req.Header.Set(name, value)
+	}
+}
+
+func (t *Transport) token(ctx context.Context, challenge bearerChallenge) (string, error) {
+	key := challenge.key()
+	if token := t.cachedToken(key); token != "" {
+		return token, nil
+	}
+
+	token, expiresAt, err := t.fetchToken(ctx, challenge)
+	if err != nil {
+		return "", err
+	}
+
+	t.mu.Lock()
+	t.tokens[key] = cachedToken{value: token, expiresAt: expiresAt}
+	t.mu.Unlock()
+	return token, nil
+}
+
+func (t *Transport) fetchToken(ctx context.Context, challenge bearerChallenge) (string, time.Time, error) {
+	tokenURL, err := url.Parse(challenge.realm)
+	if err != nil || !tokenURL.IsAbs() || (tokenURL.Scheme != "https" && tokenURL.Scheme != "http") {
+		return "", time.Time{}, fmt.Errorf("invalid token realm %q", challenge.realm)
+	}
+
+	query := tokenURL.Query()
+	if challenge.service != "" {
+		query.Set("service", challenge.service)
+	}
+	for _, scope := range challenge.scopes {
+		query.Add("scope", scope)
+	}
+	query.Set("client_id", "git-pkgs-proxy")
+	tokenURL.RawQuery = query.Encode()
+
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet, tokenURL.String(), nil)
+	if err != nil {
+		return "", time.Time{}, err
+	}
+
+	client := &http.Client{Transport: configuredTransport{parent: t}}
+	resp, err := client.Do(req)
+	if err != nil {
+		return "", time.Time{}, fmt.Errorf("requesting token: %w", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	if resp.StatusCode < http.StatusOK || resp.StatusCode >= http.StatusMultipleChoices {
+		body, _ := io.ReadAll(io.LimitReader(resp.Body, maxTokenResponseSize))
+		return "", time.Time{}, fmt.Errorf("token service returned %d: %s", resp.StatusCode, strings.TrimSpace(string(body)))
+	}
+
+	var payload tokenResponse
+	if err := json.NewDecoder(io.LimitReader(resp.Body, maxTokenResponseSize)).Decode(&payload); err != nil {
+		return "", time.Time{}, fmt.Errorf("decoding token response: %w", err)
+	}
+	token := payload.Token
+	if token == "" {
+		token = payload.AccessToken
+	}
+	if token == "" {
+		return "", time.Time{}, fmt.Errorf("token response did not contain a token")
+	}
+
+	issuedAt := time.Now()
+	if payload.IssuedAt != "" {
+		if parsed, parseErr := time.Parse(time.RFC3339, payload.IssuedAt); parseErr == nil {
+			issuedAt = parsed
+		}
+	}
+	lifetime := time.Duration(payload.ExpiresIn) * time.Second
+	if lifetime <= 0 {
+		lifetime = defaultTokenLifetime
+	}
+	expiresAt := issuedAt.Add(lifetime).Add(-expirySkew(lifetime))
+	return token, expiresAt, nil
+}
+
+type configuredTransport struct {
+	parent *Transport
+}
+
+func (t configuredTransport) RoundTrip(req *http.Request) (*http.Response, error) {
+	outbound := cloneRequest(req)
+	t.parent.applyConfiguredAuthentication(outbound)
+	return t.parent.base.RoundTrip(outbound)
+}
+
+func (t *Transport) cachedTokenForRequest(requestURL *url.URL) string {
+	space := registryProtectionSpace(requestURL)
+	if space == "" {
+		return ""
+	}
+
+	t.mu.Lock()
+	challenge, ok := t.challenges[space]
+	t.mu.Unlock()
+	if !ok {
+		return ""
+	}
+	return t.cachedToken(challenge.key())
+}
+
+func (t *Transport) cachedToken(key string) string {
+	now := time.Now()
+	t.mu.Lock()
+	defer t.mu.Unlock()
+
+	token, ok := t.tokens[key]
+	if !ok {
+		return ""
+	}
+	if !now.Before(token.expiresAt) {
+		delete(t.tokens, key)
+		return ""
+	}
+	return token.value
+}
+
+func (t *Transport) rememberChallenge(requestURL *url.URL, challenge bearerChallenge) {
+	space := registryProtectionSpace(requestURL)
+	if space == "" {
+		return
+	}
+	t.mu.Lock()
+	t.challenges[space] = challenge
+	t.mu.Unlock()
+}
+
+func (c bearerChallenge) key() string {
+	return c.realm + "\x00" + c.service + "\x00" + strings.Join(c.scopes, "\x00")
+}
+
+func registryProtectionSpace(u *url.URL) string {
+	const registryPrefix = "/v2/"
+	if u == nil || !strings.HasPrefix(u.Path, registryPrefix) {
+		return ""
+	}
+	rest := strings.TrimPrefix(u.Path, registryPrefix)
+	end := len(rest)
+	for _, marker := range []string{"/blobs/", "/manifests/", "/tags/", "/referrers/"} {
+		if index := strings.Index(rest, marker); index >= 0 && index < end {
+			end = index
+		}
+	}
+	if end == len(rest) || end == 0 {
+		return ""
+	}
+	return u.Scheme + "://" + u.Host + registryPrefix + rest[:end]
+}
+
+func parseBearerChallenge(values []string) (bearerChallenge, bool) {
+	for _, value := range values {
+		params, ok := bearerParameters(value)
+		if !ok || params["realm"] == "" {
+			continue
+		}
+		challenge := bearerChallenge{
+			realm:   params["realm"],
+			service: params["service"],
+		}
+		if scope := params["scope"]; scope != "" {
+			challenge.scopes = append(challenge.scopes, scope)
+		}
+		return challenge, true
+	}
+	return bearerChallenge{}, false
+}
+
+func bearerParameters(value string) (map[string]string, bool) {
+	start := findAuthScheme(value, "Bearer")
+	if start < 0 {
+		return nil, false
+	}
+	rest := value[start+len("Bearer"):]
+	params := make(map[string]string)
+	for {
+		rest = strings.TrimLeft(rest, " \t,")
+		if rest == "" {
+			break
+		}
+
+		keyEnd := strings.IndexAny(rest, "= \t,")
+		if keyEnd <= 0 {
+			break
+		}
+		key := strings.ToLower(rest[:keyEnd])
+		rest = strings.TrimLeft(rest[keyEnd:], " \t")
+		if rest == "" || rest[0] != '=' {
+			break
+		}
+		rest = strings.TrimLeft(rest[1:], " \t")
+
+		parsed, remaining, ok := parseAuthValue(rest)
+		if !ok {
+			return nil, false
+		}
+		params[key] = parsed
+		rest = remaining
+	}
+	return params, true
+}
+
+func findAuthScheme(value, scheme string) int {
+	inQuote := false
+	escaped := false
+	for index := 0; index+len(scheme) <= len(value); index++ {
+		char := value[index]
+		if escaped {
+			escaped = false
+			continue
+		}
+		if char == '\\' && inQuote {
+			escaped = true
+			continue
+		}
+		if char == '"' {
+			inQuote = !inQuote
+			continue
+		}
+		if inQuote || !strings.EqualFold(value[index:index+len(scheme)], scheme) {
+			continue
+		}
+		beforeOK := index == 0 || value[index-1] == ',' || value[index-1] == ' ' || value[index-1] == '\t'
+		after := index + len(scheme)
+		afterOK := after < len(value) && (value[after] == ' ' || value[after] == '\t')
+		if beforeOK && afterOK {
+			return index
+		}
+	}
+	return -1
+}
+
+func parseAuthValue(value string) (parsed, remaining string, ok bool) {
+	if value == "" {
+		return "", "", false
+	}
+	if value[0] != '"' {
+		end := strings.IndexAny(value, " \t,")
+		if end < 0 {
+			return value, "", true
+		}
+		return value[:end], value[end:], end > 0
+	}
+
+	var builder strings.Builder
+	escaped := false
+	for index := 1; index < len(value); index++ {
+		char := value[index]
+		if escaped {
+			builder.WriteByte(char)
+			escaped = false
+			continue
+		}
+		if char == '\\' {
+			escaped = true
+			continue
+		}
+		if char == '"' {
+			return builder.String(), value[index+1:], true
+		}
+		builder.WriteByte(char)
+	}
+	return "", "", false
+}
+
+func cloneRequest(req *http.Request) *http.Request {
+	clone := req.Clone(req.Context())
+	clone.Header = req.Header.Clone()
+	return clone
+}
+
+func canReplay(req *http.Request) bool {
+	return req.Body == nil || req.GetBody != nil
+}
+
+func cloneRequestForRetry(req *http.Request) (*http.Request, error) {
+	clone := cloneRequest(req)
+	if req.Body == nil {
+		return clone, nil
+	}
+	body, err := req.GetBody()
+	if err != nil {
+		return nil, fmt.Errorf("replaying authenticated request: %w", err)
+	}
+	clone.Body = body
+	return clone, nil
+}
+
+func expirySkew(lifetime time.Duration) time.Duration {
+	if lifetime < tokenExpirySkew*2 {
+		return lifetime / shortTokenSkewDivisor
+	}
+	return tokenExpirySkew
+}
+
+func drainAndClose(body io.ReadCloser) {
+	_, _ = io.Copy(io.Discard, io.LimitReader(body, maxTokenResponseSize))
+	_ = body.Close()
+}

internal/httpclient/transport_test.go

@@ -0,0 +1,151 @@
+package httpclient
+
+import (
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"strings"
+	"testing"
+)
+
+func TestTransportFollowsBearerChallengeAndCachesToken(t *testing.T) {
+	var registryRequests int
+	var tokenRequests int
+	var server *httptest.Server
+
+	server = httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		switch r.URL.Path {
+		case "/token":
+			tokenRequests++
+			if got := r.URL.Query().Get("service"); got != "registry.test" {
+				t.Errorf("service = %q, want %q", got, "registry.test")
+			}
+			if got := r.URL.Query().Get("scope"); got != "repository:library/test:pull" {
+				t.Errorf("scope = %q, want %q", got, "repository:library/test:pull")
+			}
+			w.Header().Set("Content-Type", "application/json")
+			_, _ = io.WriteString(w, `{"token":"registry-token","expires_in":3600}`)
+		case "/v2/library/test/blobs/sha256:first", "/v2/library/test/blobs/sha256:second":
+			registryRequests++
+			if r.Header.Get("Authorization") != "Bearer registry-token" {
+				w.Header().Set("WWW-Authenticate", `Bearer realm="`+server.URL+`/token",service="registry.test",scope="repository:library/test:pull"`)
+				http.Error(w, "authentication required", http.StatusUnauthorized)
+				return
+			}
+			_, _ = io.WriteString(w, "blob")
+		default:
+			http.NotFound(w, r)
+		}
+	}))
+	defer server.Close()
+
+	client := &http.Client{Transport: NewTransport(http.DefaultTransport, nil)}
+	for _, digest := range []string{"sha256:first", "sha256:second"} {
+		resp, err := client.Get(server.URL + "/v2/library/test/blobs/" + digest)
+		if err != nil {
+			t.Fatalf("GET %s: %v", digest, err)
+		}
+		body, readErr := io.ReadAll(resp.Body)
+		_ = resp.Body.Close()
+		if readErr != nil {
+			t.Fatalf("read %s response: %v", digest, readErr)
+		}
+		if resp.StatusCode != http.StatusOK {
+			t.Fatalf("GET %s status = %d, want %d", digest, resp.StatusCode, http.StatusOK)
+		}
+		if string(body) != "blob" {
+			t.Errorf("GET %s body = %q, want %q", digest, body, "blob")
+		}
+	}
+
+	if tokenRequests != 1 {
+		t.Errorf("token requests = %d, want 1", tokenRequests)
+	}
+	if registryRequests != 3 {
+		t.Errorf("registry requests = %d, want 3", registryRequests)
+	}
+}
+
+func TestTransportAddsConfiguredAuthentication(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if got := r.Header.Get("X-Registry-Token"); got != "configured-token" {
+			t.Errorf("X-Registry-Token = %q, want %q", got, "configured-token")
+		}
+		w.WriteHeader(http.StatusNoContent)
+	}))
+	defer server.Close()
+
+	authForURL := func(url string) (string, string) {
+		if strings.HasPrefix(url, server.URL) {
+			return "X-Registry-Token", "configured-token"
+		}
+		return "", ""
+	}
+	client := &http.Client{Transport: NewTransport(http.DefaultTransport, authForURL)}
+
+	resp, err := client.Get(server.URL + "/metadata")
+	if err != nil {
+		t.Fatalf("GET metadata: %v", err)
+	}
+	_ = resp.Body.Close()
+	if resp.StatusCode != http.StatusNoContent {
+		t.Errorf("status = %d, want %d", resp.StatusCode, http.StatusNoContent)
+	}
+}
+
+func TestTransportPreservesExplicitAuthentication(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if got := r.Header.Get("Authorization"); got != "Bearer explicit-token" {
+			t.Errorf("Authorization = %q, want %q", got, "Bearer explicit-token")
+		}
+		w.WriteHeader(http.StatusNoContent)
+	}))
+	defer server.Close()
+
+	authForURL := func(string) (string, string) {
+		return "Authorization", "Bearer configured-token"
+	}
+	client := &http.Client{Transport: NewTransport(http.DefaultTransport, authForURL)}
+	req, err := http.NewRequest(http.MethodGet, server.URL+"/artifact", nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	req.Header.Set("Authorization", "Bearer explicit-token")
+
+	resp, err := client.Do(req)
+	if err != nil {
+		t.Fatalf("GET artifact: %v", err)
+	}
+	_ = resp.Body.Close()
+	if resp.StatusCode != http.StatusNoContent {
+		t.Errorf("status = %d, want %d", resp.StatusCode, http.StatusNoContent)
+	}
+}
+
+func TestTransportDoesNotFollowBearerChallengeOutsideOCIRegistry(t *testing.T) {
+	tokenRequests := 0
+	var server *httptest.Server
+	server = httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.URL.Path == "/token" {
+			tokenRequests++
+			_, _ = io.WriteString(w, `{"token":"unexpected"}`)
+			return
+		}
+		w.Header().Set("WWW-Authenticate", `Bearer realm="`+server.URL+`/token"`)
+		http.Error(w, "authentication required", http.StatusUnauthorized)
+	}))
+	defer server.Close()
+
+	client := &http.Client{Transport: NewTransport(http.DefaultTransport, nil)}
+	resp, err := client.Get(server.URL + "/api/packages")
+	if err != nil {
+		t.Fatalf("GET API: %v", err)
+	}
+	_ = resp.Body.Close()
+	if resp.StatusCode != http.StatusUnauthorized {
+		t.Errorf("status = %d, want %d", resp.StatusCode, http.StatusUnauthorized)
+	}
+	if tokenRequests != 0 {
+		t.Errorf("token requests = %d, want 0", tokenRequests)
+	}
+}

internal/server/server.go

@@ -58,17 +58,19 @@ import (
 	"strings"
 	"time"
 
+	"github.com/git-pkgs/cooldown"
 	swaggerdoc "github.com/git-pkgs/proxy/docs/swagger"
 	"github.com/git-pkgs/proxy/internal/config"
-	"github.com/git-pkgs/cooldown"
 	"github.com/git-pkgs/proxy/internal/database"
 	"github.com/git-pkgs/proxy/internal/enrichment"
 	"github.com/git-pkgs/proxy/internal/handler"
+	upstreamhttp "github.com/git-pkgs/proxy/internal/httpclient"
 	"github.com/git-pkgs/proxy/internal/metrics"
 	"github.com/git-pkgs/proxy/internal/mirror"
 	"github.com/git-pkgs/proxy/internal/storage"
 	"github.com/git-pkgs/purl"
 	"github.com/git-pkgs/registries/fetch"
+	"github.com/git-pkgs/registries/safehttp"
 	"github.com/git-pkgs/spdx"
 	"github.com/go-chi/chi/v5"
 	"github.com/go-chi/chi/v5/middleware"
@@ -156,8 +158,18 @@ func New(cfg *config.Config, logger *slog.Logger) (*Server, error) {
 
 // Start starts the HTTP server.
 func (s *Server) Start() error {
-	// Create shared components with circuit breaker
-	baseFetcher := fetch.NewFetcher(fetch.WithAuthFunc(s.authForURL))
+	// Use one authentication-aware transport for metadata and artifacts so
+	// configured credentials and cached OCI challenges apply consistently.
+	safeClient := safehttp.New(nil, safehttp.Options{})
+	authTransport := upstreamhttp.NewTransport(safeClient.Transport, upstreamhttp.AuthFunc(s.authForURL))
+	metadataClient := *safeClient
+	metadataClient.Timeout = s.cfg.ParseHTTPTimeout()
+	metadataClient.Transport = authTransport
+	artifactClient := metadataClient
+	artifactClient.Timeout = serverWriteTimeout
+
+	// Create shared components with circuit breaker.
+	baseFetcher := fetch.NewFetcher(fetch.WithHTTPClient(&artifactClient))
 	fetcher := fetch.NewCircuitBreakerFetcher(baseFetcher)
 	resolver := fetch.NewResolver()
 	cd := &cooldown.Config{
@@ -166,7 +178,7 @@ func (s *Server) Start() error {
 		Packages:   s.cfg.Cooldown.Packages,
 	}
 	proxy := handler.NewProxy(s.db, s.storage, fetcher, resolver, s.logger)
-	proxy.HTTPClient.Timeout = s.cfg.ParseHTTPTimeout()
+	proxy.HTTPClient = &metadataClient
 	proxy.Cooldown = cd
 	proxy.CacheMetadata = s.cfg.CacheMetadata
 	proxy.MetadataTTL = s.cfg.ParseMetadataTTL()