Put this PR's TODO.md entry back at the top of Completed Steps

The rebase onto next placed it under the entry for the negative cache
cleanup, as union merge keeps next's lines first.

Model: opus-5-5

README.md

@@ -200,9 +200,10 @@ path under `/v1/` answers 200, in maintenance mode too.
   `image_requests_per_minute` (below); 415 when the upstream answers with a
   `Content-Type` that is not one of the source formats (below), or with an image
   whose first bytes libvips reads as another format; 502 when the upstream
-  answered with an error status, and for 5 minutes after that for the same
+  answered with an error status, and for 5 minutes after that for an image of
-  source URL; 503 when pixa is busy or in maintenance mode; 500 for any other
+  the same source URL that pixa can neither serve from its cache nor make from
-  failure.
+  the source image still in its cache; 503 when pixa is busy or in maintenance
+  mode; 500 for any other failure.
 - `GET` or `HEAD` `/v1/e/<token>/<name>` — an image through an encrypted URL
   (see Encrypted URLs). Needs: nothing but the URL. Answers: 200; 304 when
   `If-None-Match` matches the image's `ETag`; 400 for a token that does not
@@ -313,9 +314,26 @@ cache at once, they share one upstream fetch (or one read of the cached source)
 and one transcode: the first request does the work, and the others wait for its
 image or its error, holding no upstream connection or processing slot of their
 own. A waiting request stops waiting when its own client goes away. The work
-goes on for the others even if the first request's client goes away, until that
+goes on for the others even if the first request's client goes away. The shared
-request's `downstream_timeout` ends. The shared fetch sends the first request's
+fetch sends the first request's ID upstream, and the lines logged for the fetch
-ID upstream, and the lines logged for the fetch and the transcode carry that ID.
+and the transcode carry that ID.
+
+A transcode whose request's `downstream_timeout` has ended (for a shared one,
+the first request's) stops waiting for a processing slot, or, once it has one,
+gives it back without beginning to encode. A request waiting for a shared
+transcode that stops this way is answered 503 with the error
+`server busy, try again later`, though its own `downstream_timeout` may not have
+ended. govips gives pixa no way to stop libvips once an encode has begun, so an
+encode keeps its slot until it finishes, which can be after
+`downstream_timeout`. The limit of 8192 on each side of the source and of the
+output bounds how long that takes. With one libvips thread, as pixad runs it,
+encoding 8192x8192 random pixels takes up to about 1 second as JPEG, 15 as PNG,
+16 as GIF, 63 as WebP, 110 as AVIF and 96 as JPEG XL, the slowest of 8 or 16
+bits per sample, with or without an alpha channel. WebP, AVIF and JPEG XL are
+that slow only with an alpha channel: 8-bit RGB takes about 44, 53 and 28
+seconds. Decoding such a source adds up to about 11 seconds. A WebP, AVIF or
+JPEG XL encode can therefore hold its slot past the default `downstream_timeout`
+of 60 seconds.
 
 The login form (`POST /`) is limited to 5 attempts per minute per client
 address, counting an IPv6 client by its /64; an attempt over the limit is
@@ -418,7 +436,9 @@ HMAC-SHA256(secret, "host:path:query:width:height:format:expiration:quality:fit"
 
 Where:
 
-- `host` — source origin hostname (e.g. `cdn.example.com`)
+- `host` — source host as the URL writes it up to the first `/`, in lower case,
+  keeping an IPv6 address's brackets and any `:` and port after it (e.g.
+  `cdn.example.com`, `cdn.example.com:8443`, `[2001:db8::1]:8443`)
 - `path` — source path (e.g. `/photos/cat.jpg`), with each `%` written as `%25`
   and each `:` as `%3A`, so `/photos/a:b.jpg` is signed as `/photos/a%3Ab.jpg`
 - `query` — source query string, empty string if none, with `%` and `:` written
@@ -473,6 +493,12 @@ entry that is neither a host name (letters, digits, hyphens, underscores and
 dots, with at most one leading dot) nor an IP address, such as one with a port
 or a `*.` wildcard, aborts startup.
 
+pixa lower-cases the host of a `/v1/image/` URL before anything else uses it, so
+`CDN.Example.com` is matched, fetched, cached and counted against
+`upstream_connections_per_host` as `cdn.example.com`. Such a URL whose host has
+a port, as in `cdn.example.com:8443`, or a `:` with no port, needs a signature
+even when the host is allowlisted. A host holding `@` is refused with 400.
+
 ### Configuration
 
 Every setting can be given as an environment variable, in a YAML config file

TODO.md

@@ -30,6 +30,56 @@ P2: security: per-origin rate limiting
 
 # Completed Steps
 
+- 2026-10-15 a transcode stops once its request's `downstream_timeout` has
+  ended, unless it has begun encoding (closes #243): the image processor looked
+  at its context only while it waited for a processing slot, so an image was
+  decoded and encoded, holding the slot, however long after its request's
+  deadline that took. `Process` now returns the context's error, and gives the
+  slot back, when the context has ended by the time it has the slot or before it
+  encodes. A request that waited for a shared transcode stopped at the first
+  request's deadline is answered 503 `server busy, try again later`, not 500,
+  though its own `downstream_timeout` may not have ended. govips gives pixa no
+  way to stop libvips once an encode has begun, so that encode keeps its slot
+  until it finishes; the limit of 8192 on each side of the source and of the
+  output bounds how long that takes. With one libvips thread, 8192x8192 random
+  pixels take up to about 1 second to encode as JPEG, 15 as PNG, 16 as GIF, 63
+  as WebP, 110 as AVIF and 96 as JPEG XL, the last three with an alpha channel,
+  plus up to about 11 seconds to decode the source; `README.md` gives these
+  times and no longer says the work stops when `downstream_timeout` ends. The
+  settings of the WebP, AVIF and JPEG XL encoders, which can hold a slot past
+  the default `downstream_timeout` of 60 seconds, are unchanged.
+- 2026-10-15 expired negative cache rows are removed on a schedule (closes
+  #244): the row of a failed fetch, which makes pixa answer 502 for that source
+  URL for 5 minutes, was deleted only when the same URL was requested again
+  after that, so a client asking for a new missing path each time added rows
+  that stayed for good. The eviction goroutine now calls `CleanExpired` at
+  startup and on each periodic tick, every 5 minutes in pixad, so a row stays at
+  most about 10 minutes. `CleanExpired` deletes at most 1000 rows per statement,
+  so a request waits behind 1000 deletions at most, however many rows have
+  expired. The goroutine runs with the disk cache disabled
+  (`cache_max_bytes: 0`) too, where it does nothing else, as the negative cache
+  is used either way.
+- 2026-10-15 a cached variant is served while its source URL is in the negative
+  cache (closes #245): `Get` checked the negative cache before the variant
+  cache, so once a fetch of the source failed, as one does when another variant
+  misses after the source was evicted and the upstream is down, every variant of
+  that source answered 502 for 5 minutes, also one on disk or one that could be
+  made from the cached source. The negative cache is now checked only just
+  before a fetch from the upstream, so a cached variant is served and a variant
+  not in the cache is made from the cached source when there is one. `README.md`
+  says so under `/v1/image/`. A refusal from the negative cache now counts as a
+  miss, as any other request that misses the variant cache does.
+- 2026-10-15 the host of a `/v1/image/` URL is lower-cased, and one with a port
+  needs a signature (closes #246): with `cdn.example.com` allowlisted,
+  `CDN.Example.com` and `cdn.example.com:8443` passed the allowlist too, and
+  each spelling was fetched and cached on its own and had connections of its own
+  under `upstream_connections_per_host`. The image URL parser now lower-cases
+  the host and refuses one holding `@`, which a URL reads as a user name and
+  password, with 400. A host with a port, or with a `:` and no port, needs a
+  signature even when it is allowlisted. That is checked in the image service,
+  not in `allowlist.IsAllowed`, which also matches `referer_blocklist`, where a
+  `Referer` is blocked whatever its port. A URL is signed over its host as it
+  writes it, in lower case, with any IPv6 brackets, `:` and port kept.
 - 2026-10-15 a `:` in the source path or query no longer moves where the path
   ends and the query begins (closes #247): the signed data and the cache key
   joined host, path and query with `:` and no escaping, so a URL signed for
@@ -501,11 +551,11 @@ P2: security: per-origin rate limiting
   cancellation but keeps its deadline, and the others wait for its image or
   error holding no upstream connection or processing slot, and stop waiting when
   their own context ends; the request doing the processing waits for it even
-  then, up to its deadline; a request whose context has already ended starts
+  then, until it ends, which can be after its deadline; a request whose context
-  nothing; each request counts one miss, and the processing counts its fetch and
+  has already ended starts nothing; each request counts one miss, and the
-  transcode once; a panic while processing is reported to Sentry when
+  processing counts its fetch and transcode once; a panic while processing is
-  `sentry_dsn` is set and becomes an error for every waiting request instead of
+  reported to Sentry when `sentry_dsn` is set and becomes an error for every
-  stopping pixad; documented in `README.md`.
+  waiting request instead of stopping pixad; documented in `README.md`.
 - 2026-09-29 only the image routes send CORS headers (closes #98): the CORS
   middleware, with the `access_control_allow_origin` origin, moved from the
   router root onto a `/v1` subrouter holding `/v1/image/` and `/v1/e/`, where it

internal/handlers/handlers.go

@@ -124,7 +124,8 @@ func (s *Handlers) initImageService() error {
 	s.imgCache = cache
 
 	// Background eviction: startup reconciliation, then periodic and
-	// write-pressure passes. No-op when the disk cache is disabled.
+	// write-pressure passes, and the removal of expired negative cache
+	// rows, which is all it does when the disk cache is disabled.
 	cache.StartEviction(imgcache.DefaultEvictionInterval)
 
 	// Writes the counts requests could not write by their deadline

internal/handlers/image.go

@@ -240,7 +240,8 @@ func (s *Handlers) respondImageError(
 	}
 
 	if errors.Is(err, httpfetcher.ErrTooManyConnections) ||
-		errors.Is(err, imageprocessor.ErrTooManyImages) {
+		errors.Is(err, imageprocessor.ErrTooManyImages) ||
+		errors.Is(err, imgcache.ErrProcessingTimedOut) {
 		s.respondError(w, "server busy, try again later",
 			http.StatusServiceUnavailable)
 

internal/handlers/imageenc.go

@@ -158,7 +158,8 @@ func (s *Handlers) handleImageError(w http.ResponseWriter, err error) {
 	case errors.Is(err, httpfetcher.ErrUpstreamTimeout):
 		s.respondError(w, "upstream timeout", http.StatusGatewayTimeout)
 	case errors.Is(err, httpfetcher.ErrTooManyConnections),
-		errors.Is(err, imageprocessor.ErrTooManyImages):
+		errors.Is(err, imageprocessor.ErrTooManyImages),
+		errors.Is(err, imgcache.ErrProcessingTimedOut):
 		s.respondError(w, "server busy, try again later",
 			http.StatusServiceUnavailable)
 	case errors.Is(err, httpfetcher.ErrInvalidContentType),

internal/handlers/server_busy_internal_test.go

@@ -1,6 +1,7 @@
 package handlers
 
 import (
+	"context"
 	"fmt"
 	"log/slog"
 	"net/http"
@@ -47,3 +48,40 @@ func TestServerBusyAnswers503(t *testing.T) {
 		}
 	}
 }
+
+// TestProcessingTimedOutAnswers503 checks that respondImageError and
+// handleImageError, which answer the errors of the two image routes, answer
+// 503 with the server busy error when the image service reports that
+// processing stopped at the deadline of the request doing it, wrapped as the
+// service wraps it. A request that waited for that processing gets this error
+// while its own deadline may have time left. The request's source only goes
+// into a log line, so it is left empty.
+func TestProcessingTimedOutAnswers503(t *testing.T) {
+	t.Parallel()
+
+	h := &Handlers{log: slog.New(slog.DiscardHandler)}
+	err := fmt.Errorf("%w: failed to encode: %w",
+		imgcache.ErrProcessingTimedOut, context.DeadlineExceeded)
+
+	plain := httptest.NewRecorder()
+	h.respondImageError(plain, &imgcache.ImageRequest{}, err)
+
+	encrypted := httptest.NewRecorder()
+	h.handleImageError(encrypted, err)
+
+	for name, rec := range map[string]*httptest.ResponseRecorder{
+		"respondImageError": plain, "handleImageError": encrypted,
+	} {
+		t.Logf("%s: status = %d, body = %q", name, rec.Code, rec.Body.String())
+
+		if rec.Code != http.StatusServiceUnavailable {
+			t.Errorf("%s: status = %d, want %d",
+				name, rec.Code, http.StatusServiceUnavailable)
+		}
+
+		if !strings.Contains(rec.Body.String(), "server busy, try again later") {
+			t.Errorf("%s: body = %q, want the server busy error",
+				name, rec.Body.String())
+		}
+	}
+}

internal/imageprocessor/deadline_internal_test.go

@@ -0,0 +1,106 @@
+package imageprocessor
+
+import (
+	"bytes"
+	"context"
+	"errors"
+	"io"
+	"testing"
+	"time"
+)
+
+// readerAfterDeadline is a Process input whose first Read waits until done
+// is closed, so the deadline passes after Process has taken its slot and
+// before it encodes.
+type readerAfterDeadline struct {
+	data   *bytes.Reader
+	done   <-chan struct{}
+	waited bool
+}
+
+func (r *readerAfterDeadline) Read(p []byte) (int, error) {
+	if !r.waited {
+		r.waited = true
+
+		<-r.done
+	}
+
+	return r.data.Read(p)
+}
+
+// inputNotToBeRead is a Process input that fails the test when it is read.
+type inputNotToBeRead struct {
+	t *testing.T
+}
+
+func (r inputNotToBeRead) Read([]byte) (int, error) {
+	r.t.Error("Process read its input although its deadline had passed")
+
+	return 0, io.EOF
+}
+
+// TestProcessStopsWhenDeadlinePassed checks that Process returns
+// context.DeadlineExceeded, and holds no slot afterwards, when its context's
+// deadline has passed before it starts, then without reading its input, or
+// while it reads its input. govips gives pixa no way to stop libvips once an
+// encode has begun, so Process must not begin one for a request that has
+// ended.
+func TestProcessStopsWhenDeadlinePassed(t *testing.T) {
+	t.Parallel()
+
+	input := createTestJPEG(t, 50, 50)
+
+	t.Run("before Process starts", func(t *testing.T) {
+		t.Parallel()
+
+		ctx, cancel := context.WithDeadline(t.Context(),
+			time.Now().Add(-time.Second))
+		defer cancel()
+
+		// With a slot free, the select in acquireSlot takes the slot or sees
+		// the ended context at random, so Process is called many times
+		for range 100 {
+			checkProcessStopsAtDeadline(ctx, t, inputNotToBeRead{t: t})
+		}
+	})
+
+	t.Run("while Process reads its input", func(t *testing.T) {
+		t.Parallel()
+
+		ctx, cancel := context.WithTimeout(t.Context(), 100*time.Millisecond)
+		defer cancel()
+
+		checkProcessStopsAtDeadline(ctx, t, &readerAfterDeadline{
+			data: bytes.NewReader(input), done: ctx.Done(),
+		})
+	})
+}
+
+// checkProcessStopsAtDeadline runs Process on input with ctx, whose deadline
+// has passed by the time Process could encode, and fails the test unless
+// Process returns context.DeadlineExceeded and gives its slot back.
+func checkProcessStopsAtDeadline(
+	ctx context.Context, t *testing.T, input io.Reader,
+) {
+	t.Helper()
+
+	proc := New(Params{MaxConcurrentProcessing: 1})
+
+	result, err := proc.Process(ctx, input, smallJPEGRequest())
+	if result != nil {
+		t.Logf("Process() made a %dx%d image after its deadline passed",
+			result.Width, result.Height)
+
+		_ = result.Content.Close()
+	}
+
+	t.Logf("Process() error = %v", err)
+
+	if !errors.Is(err, context.DeadlineExceeded) {
+		t.Errorf("Process() error = %v, want context.DeadlineExceeded", err)
+	}
+
+	if held := len(proc.processingSemaphore); held != 0 {
+		t.Errorf("%d slots still held after Process() returned", held)
+	}
+}

internal/imageprocessor/imageprocessor.go

@@ -208,7 +208,10 @@ func New(params Params) *ImageProcessor {
 // Process transforms an image according to the request. When
 // MaxConcurrentProcessing images are already being processed, it waits up
 // to ProcessingWaitTimeout for one to finish, then fails with
-// ErrTooManyImages.
+// ErrTooManyImages. When ctx has ended once Process has a slot, or before it
+// encodes, it returns ctx's error and gives the slot back. govips gives pixa
+// no way to stop libvips once an encode has begun, so an encode keeps its
+// slot until it finishes.
 func (p *ImageProcessor) Process(
 	ctx context.Context,
 	input io.Reader,
@@ -290,7 +293,7 @@ func (p *ImageProcessor) Process(
 	}
 
 	// Encode to target format
-	output, err := p.encode(img, outputFormat, req.Quality)
+	output, err := p.encode(ctx, img, outputFormat, req.Quality)
 	if err != nil {
 		return nil, fmt.Errorf("failed to encode: %w", err)
 	}
@@ -417,25 +420,28 @@ func (p *ImageProcessor) WaitForProcessing(ctx context.Context) int {
 
 // acquireSlot takes a slot in processingSemaphore, waiting at most
 // processingWaitTimeout for one to free up, and returns the func that gives
-// it back. A free slot is taken even when ctx has ended; only the wait for
+// it back. When ctx has ended by the time it has a slot, it gives the slot
-// one stops when ctx ends, as the rest of Process does not check ctx.
+// back and returns ctx's error.
 func (p *ImageProcessor) acquireSlot(ctx context.Context) (func(), error) {
-	release := func() { <-p.processingSemaphore }
-
 	select {
 	case p.processingSemaphore <- struct{}{}:
-		return release, nil
-	default:
-	}
-
-	select {
-	case p.processingSemaphore <- struct{}{}:
-		return release, nil
 	case <-time.After(p.processingWaitTimeout):
 		return nil, ErrTooManyImages
 	case <-ctx.Done():
 		return nil, ctx.Err()
 	}
+
+	release := func() { <-p.processingSemaphore }
+
+	// select takes the slot even when ctx has ended at the same moment
+	err := ctx.Err()
+	if err != nil {
+		release()
+
+		return nil, err
+	}
+
+	return release, nil
 }
 
 // detectFormat returns the format string for a govips image type.
@@ -527,10 +533,17 @@ func (p *ImageProcessor) resize(
 
 const defaultQuality = 85
 
-// encode encodes an image to the specified format.
+// encode encodes an image to the specified format. govips gives pixa no way
+// to stop libvips once an encode has begun, so when ctx has ended encode
+// returns ctx's error without beginning one.
 func (p *ImageProcessor) encode(
-	img *vips.ImageRef, format Format, quality int,
+	ctx context.Context, img *vips.ImageRef, format Format, quality int,
 ) ([]byte, error) {
+	err := ctx.Err()
+	if err != nil {
+		return nil, err
+	}
+
 	if quality <= 0 {
 		quality = defaultQuality
 	}
@@ -540,7 +553,7 @@ func (p *ImageProcessor) encode(
 	// libvips' built-in profile; govips' own sRGB path variable is set on
 	// first use but read without a lock, so concurrent requests race on it.
 	if img.HasICCProfile() {
-		err := img.TransformICCProfileWithFallback("srgb", "srgb")
+		err = img.TransformICCProfileWithFallback("srgb", "srgb")
 		if err != nil {
 			return nil, fmt.Errorf("failed to convert to sRGB: %w", err)
 		}
@@ -632,10 +645,11 @@ func exportWebP(img *vips.ImageRef, quality int) ([]byte, error) {
 
 // avifEffort is the AVIF effort, from 0 (fastest) to 9; 1 is the lowest
 // govips can set. With one thread, as pixad runs libvips, 1 takes about 51
-// seconds to save an 8192x8192 image of random pixels, the worst case,
+// seconds to save an 8192x8192 RGB image of random pixels, and about 110
-// against the default downstream_timeout of 60 seconds. On an image of
+// with an alpha channel, the worst case, against the default
-// milder noise, which 1 saves in about 12 seconds, 2 takes nearly a minute
+// downstream_timeout of 60 seconds. On an image of milder noise, which 1
-// and libvips' default, 4, takes minutes.
+// saves in about 12 seconds, 2 takes nearly a minute and libvips' default,
+// 4, takes minutes.
 const avifEffort = 1
 
 // avifBitdepth is the AVIF bit depth, 8 bits per sample for every image.

internal/imgcache/cache.go

@@ -32,6 +32,12 @@ const httpStatusOK = 200
 // variant not among them is served as before, reading its .meta file.
 const metaCacheSize = 10000
 
+// cleanExpiredBatchSize is the most expired negative cache rows one
+// statement of CleanExpired deletes. Each batch is a statement of its
+// own, so a request waits behind one batch at most, however many rows
+// have expired.
+const cleanExpiredBatchSize = 1000
+
 // CacheConfig holds cache configuration.
 type CacheConfig struct {
 	StateDir    string
@@ -50,8 +56,9 @@ type CacheConfig struct {
 
 	// DisableDiskCache turns the disk cache off entirely: no cache
 	// directories are created, lookups always miss, stores are
-	// no-ops, and no eviction machinery runs. The config layer sets
+	// no-ops, and the eviction goroutine only removes the expired
-	// this when the operator configures cache_max_bytes: 0.
+	// negative cache rows. The config layer sets this when the
+	// operator configures cache_max_bytes: 0.
 	DisableDiskCache bool
 
 	// Logger receives accounting and eviction log output. A nil
@@ -482,17 +489,27 @@ func (c *Cache) GetSourceContent(
 	return c.srcContent.LoadWithSize(contentHash)
 }
 
-// CleanExpired removes expired entries from the cache.
+// CleanExpired removes the negative cache rows past their expiry, one
+// batch per statement, until none is left. Once ctx ends it starts no
+// further batch and returns ctx's error. The eviction goroutine calls it
+// at startup and on every periodic tick, so a row stays about
+// NegativeTTL plus one eviction interval, whether or not its URL is
+// requested again.
 func (c *Cache) CleanExpired(ctx context.Context) error {
-	// Clean expired negative cache entries
+	for {
-	_, err := c.db.ExecContext(ctx, `
+		if ctx.Err() != nil {
-		DELETE FROM negative_cache WHERE expires_at < CURRENT_TIMESTAMP
+			return ctx.Err()
-	`)
+		}
-	if err != nil {
-		return fmt.Errorf("failed to clean negative cache: %w", err)
-	}
 
-	return nil
+		deleted, err := c.cleanExpiredBatch(ctx)
+		if err != nil {
+			return err
+		}
+
+		if deleted < cleanExpiredBatchSize {
+			return nil
+		}
+	}
 }
 
 // Stats returns cache statistics.
@@ -756,3 +773,27 @@ func (c *Cache) checkNegativeCache(
 
 	return true, nil
 }
+
+// cleanExpiredBatch deletes up to cleanExpiredBatchSize negative cache
+// rows past their expiry in one statement, and returns how many it
+// deleted. DELETE ... LIMIT needs a SQLite build option, so the subquery
+// picks the rows.
+func (c *Cache) cleanExpiredBatch(ctx context.Context) (int64, error) {
+	result, err := c.db.ExecContext(ctx, `
+		DELETE FROM negative_cache WHERE id IN (
+			SELECT id FROM negative_cache
+			WHERE expires_at < CURRENT_TIMESTAMP
+			LIMIT ?
+		)
+	`, cleanExpiredBatchSize)
+	if err != nil {
+		return 0, fmt.Errorf("failed to clean negative cache: %w", err)
+	}
+
+	deleted, err := result.RowsAffected()
+	if err != nil {
+		return 0, fmt.Errorf("failed to count cleaned negative cache rows: %w", err)
+	}
+
+	return deleted, nil
+}

internal/imgcache/concurrent_misses_internal_test.go

@@ -15,6 +15,7 @@ import (
 
 	"github.com/getsentry/sentry-go"
 	"sneak.berlin/go/pixa/internal/httpfetcher"
+	"sneak.berlin/go/pixa/internal/imageprocessor"
 	"sneak.berlin/go/pixa/internal/magic"
 )
 
@@ -435,6 +436,47 @@ func TestService_Get_ReturnsByItsDeadline(t *testing.T) {
 	}
 }
 
+// TestService_Get_WaiterGetsProcessingTimedOut has a request with no deadline
+// join the held fetch of a first request with a short one. With the only
+// processing slot held, the first request's transcode waits for it until the
+// first request's deadline ends, and stops then. The waiting request, whose
+// own context has not ended, must get ErrProcessingTimedOut, which the image
+// routes answer 503 as when pixa is busy.
+func TestService_Get_WaiterGetsProcessingTimedOut(t *testing.T) {
+	t.Parallel()
+
+	svc, fixtures, fetcher := setupHeldFetchService(t)
+	svc.processor = imageprocessor.New(
+		imageprocessor.Params{MaxConcurrentProcessing: 1},
+	)
+
+	holdProcessingSlot(t, svc.processor)
+
+	const firstTimeout = 500 * time.Millisecond
+
+	firstCtx, cancelFirst := context.WithTimeout(t.Context(), firstTimeout)
+	defer cancelFirst()
+
+	first := startGet(firstCtx, svc, photoVariant(fixtures, 85, FitCover))
+
+	<-fetcher.started
+
+	waiter := startGet(t.Context(), svc, photoVariant(fixtures, 85, FitCover))
+
+	time.Sleep(arrivalWait)
+	fetcher.releaseFetches()
+
+	t.Logf("first request: Get() error = %v", (<-first).err)
+
+	got := <-waiter
+	t.Logf("waiting request: Get() error = %v", got.err)
+
+	if !errors.Is(got.err, ErrProcessingTimedOut) {
+		t.Errorf("waiting request: Get() error = %v, want %v",
+			got.err, ErrProcessingTimedOut)
+	}
+}
+
 // panickingFetcher panics on every fetch.
 type panickingFetcher struct{}
 

internal/imgcache/eviction.go

@@ -437,14 +437,16 @@ func (c *Cache) notifyWritePressure() {
 }
 
 // StartEviction launches the background eviction goroutine, which
-// reconciles the database accounting with the cache directories at
+// reconciles the database accounting with the cache directories and
-// startup and again on every periodic tick thereafter, and evicts to
+// removes the expired negative cache rows at startup and again on every
-// the configured limit on the given periodic interval and on
+// periodic tick thereafter, and evicts to the configured limit on the
-// write-pressure notifications. It is a no-op on a disabled cache or
+// given periodic interval and on write-pressure notifications. On a
-// when already started. The goroutine outlives the caller, so it runs
+// disabled cache it only removes the expired negative cache rows, as
-// with its own context, which StopEviction cancels.
+// the negative cache is used either way. It is a no-op when already
+// started. The goroutine outlives the caller, so it runs with its own
+// context, which StopEviction cancels.
 func (c *Cache) StartEviction(interval time.Duration) {
-	if c.disabled || c.evictionCancel != nil {
+	if c.evictionCancel != nil {
 		return
 	}
 
@@ -480,6 +482,7 @@ func (c *Cache) evictionLoop(ctx context.Context, interval time.Duration) {
 	defer close(c.evictionDone)
 
 	c.runReconciliationPass(ctx)
+	c.runCleanExpired(ctx)
 	c.runEvictionPass(ctx)
 
 	ticker := time.NewTicker(interval)
@@ -500,6 +503,7 @@ func (c *Cache) evictionLoop(ctx context.Context, interval time.Duration) {
 			// unaccounted for to one interval, on a process that is
 			// already running this loop regardless.
 			c.runReconciliationPass(ctx)
+			c.runCleanExpired(ctx)
 		case <-c.evictionPressure:
 		}
 
@@ -535,6 +539,20 @@ func (c *Cache) runReconciliationPass(ctx context.Context) {
 	}
 }
 
+// runCleanExpired runs CleanExpired, logging a failure instead of
+// propagating it (the loop must keep running). It does nothing once ctx
+// is cancelled.
+func (c *Cache) runCleanExpired(ctx context.Context) {
+	if ctx.Err() != nil {
+		return
+	}
+
+	err := c.CleanExpired(ctx)
+	if err != nil {
+		c.log.Warn("negative cache cleanup failed", "error", err)
+	}
+}
+
 // reconcileAccounting synchronizes the database size accounting with
 // the actual contents of the cache directories. It runs at startup and
 // again on every periodic eviction tick thereafter, off the request

internal/imgcache/negative_cache_internal_test.go

@@ -3,6 +3,7 @@ package imgcache
 import (
 	"context"
 	"errors"
+	"strconv"
 	"testing"
 	"time"
 )
@@ -94,6 +95,307 @@ func TestNegativeCache_Expired(t *testing.T) {
 	}
 }
 
+// TestService_Get_ServesCachedVariantOfNegativeCachedURL caches a variant of
+// the test photo, then keeps a failed fetch of the photo's URL in the negative
+// cache, as a failed fetch for another variant does once the source has been
+// evicted. The cached variant is still served, and a variant not in the cache
+// is made from the cached source. Once the source is evicted, a variant not in
+// the cache needs a fetch and is refused.
+func TestService_Get_ServesCachedVariantOfNegativeCachedURL(t *testing.T) {
+	t.Parallel()
+
+	svc, fixtures := SetupTestService(t)
+
+	resp, err := svc.Get(t.Context(), photoVariant(fixtures, 85, FitCover))
+	if err != nil {
+		t.Fatalf("Get() first request error = %v", err)
+	}
+
+	_ = resp.Content.Close()
+
+	err = svc.cache.StoreNegative(t.Context(), photoVariant(fixtures, 85, FitCover),
+		httpStatusBadGateway, "upstream answered 503")
+	if err != nil {
+		t.Fatalf("StoreNegative() error = %v", err)
+	}
+
+	resp, err = svc.Get(t.Context(), photoVariant(fixtures, 85, FitCover))
+	if err != nil {
+		t.Fatalf("Get() of the cached variant error = %v", err)
+	}
+
+	_ = resp.Content.Close()
+
+	if resp.CacheStatus != CacheHit {
+		t.Errorf("cached variant CacheStatus = %q, want %q",
+			resp.CacheStatus, CacheHit)
+	}
+
+	resp, err = svc.Get(t.Context(), photoVariant(fixtures, 40, FitCover))
+	t.Logf("Get() of a variant made from the cached source: error = %v", err)
+
+	if err != nil {
+		t.Fatalf("Get() of a variant made from the cached source error = %v", err)
+	}
+
+	_ = resp.Content.Close()
+
+	contentHash, _, err := svc.cache.LookupSource(t.Context(),
+		photoVariant(fixtures, 85, FitCover))
+	if err != nil || contentHash == "" {
+		t.Fatalf("LookupSource() = %q, %v, want the cached source", contentHash, err)
+	}
+
+	err = svc.cache.evictSourceBlob(t.Context(), contentHash)
+	if err != nil {
+		t.Fatalf("evictSourceBlob() error = %v", err)
+	}
+
+	_, err = svc.Get(t.Context(), photoVariant(fixtures, 60, FitCover))
+	t.Logf("Get() of a variant whose source was evicted: error = %v", err)
+
+	if !errors.Is(err, ErrNegativeCached) {
+		t.Errorf("Get() of a variant whose source was evicted error = %v, want %v",
+			err, ErrNegativeCached)
+	}
+}
+
+// TestEvictionLoopRemovesExpiredNegativeCacheRows stores a failed fetch
+// that expires a second later and starts the eviction loop with a short
+// interval: a later tick must remove its row although its URL is never
+// requested again, and must keep a row that has not expired. It runs
+// with the disk cache enabled and disabled, as the negative cache is
+// used either way.
+func TestEvictionLoopRemovesExpiredNegativeCacheRows(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name             string
+		disableDiskCache bool
+	}{
+		{name: "disk cache enabled", disableDiskCache: false},
+		{name: "disk cache disabled", disableDiskCache: true},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			cache, err := NewCache(evictionTestDB(t), CacheConfig{
+				StateDir:         t.TempDir(),
+				NegativeTTL:      time.Second,
+				DisableDiskCache: tt.disableDiskCache,
+			})
+			if err != nil {
+				t.Fatalf("failed to create cache: %v", err)
+			}
+
+			expired := &ImageRequest{
+				SourceHost: testHostExample, SourcePath: "/gone.jpg",
+			}
+
+			err = cache.StoreNegative(t.Context(), expired, 404, "not found")
+			if err != nil {
+				t.Fatalf("StoreNegative failed: %v", err)
+			}
+
+			const notExpiredPath = "/later.jpg"
+
+			_, err = cache.db.ExecContext(t.Context(), `
+				INSERT INTO negative_cache
+					(source_host, source_path, status_code, expires_at)
+				VALUES (?, ?, 404, datetime('now', '+1 hour'))
+			`, testHostExample, notExpiredPath)
+			if err != nil {
+				t.Fatalf("failed to insert a row that has not expired: %v", err)
+			}
+
+			started := time.Now()
+
+			cache.StartEviction(100 * time.Millisecond)
+			defer func() { _ = cache.StopEviction(t.Context()) }()
+
+			for negativeCacheRowCount(t, cache, expired.SourcePath) > 0 {
+				if time.Since(started) > 10*time.Second {
+					t.Fatal("the expired row is still in negative_cache")
+				}
+
+				time.Sleep(50 * time.Millisecond)
+			}
+
+			t.Logf("the expired row was removed %s after the loop started",
+				time.Since(started))
+
+			if negativeCacheRowCount(t, cache, notExpiredPath) != 1 {
+				t.Error("the row that has not expired was removed")
+			}
+		})
+	}
+}
+
+// negativeCacheRowCount returns how many negative_cache rows hold
+// sourcePath.
+func negativeCacheRowCount(tb testing.TB, cache *Cache, sourcePath string) int {
+	tb.Helper()
+
+	var count int
+
+	err := cache.db.QueryRowContext(tb.Context(),
+		`SELECT COUNT(*) FROM negative_cache WHERE source_path = ?`,
+		sourcePath,
+	).Scan(&count)
+	if err != nil {
+		tb.Fatalf("failed to count negative_cache rows: %v", err)
+	}
+
+	return count
+}
+
+// TestCleanExpiredDeletesInBatches stores one expired negative cache row
+// more than one batch holds, and one row that has not expired. One
+// statement must delete one batch and no more, so a request waits behind
+// one batch at most; CleanExpired must then remove the expired row left
+// over and keep the row that has not expired.
+func TestCleanExpiredDeletesInBatches(t *testing.T) {
+	t.Parallel()
+
+	cache, err := NewCache(evictionTestDB(t), CacheConfig{StateDir: t.TempDir()})
+	if err != nil {
+		t.Fatalf("failed to create cache: %v", err)
+	}
+
+	ctx := t.Context()
+
+	insertExpiredNegativeCacheRows(t, cache, cleanExpiredBatchSize+1)
+
+	const notExpiredPath = "/later.jpg"
+
+	_, err = cache.db.ExecContext(ctx, `
+		INSERT INTO negative_cache
+			(source_host, source_path, status_code, expires_at)
+		VALUES (?, ?, 404, datetime('now', '+1 hour'))
+	`, testHostExample, notExpiredPath)
+	if err != nil {
+		t.Fatalf("failed to insert a row that has not expired: %v", err)
+	}
+
+	deleted, err := cache.cleanExpiredBatch(ctx)
+	if err != nil {
+		t.Fatalf("cleanExpiredBatch failed: %v", err)
+	}
+
+	t.Logf("one statement deleted %d of %d expired rows",
+		deleted, cleanExpiredBatchSize+1)
+
+	if deleted != cleanExpiredBatchSize {
+		t.Errorf("one statement deleted %d rows, want %d",
+			deleted, cleanExpiredBatchSize)
+	}
+
+	err = cache.CleanExpired(ctx)
+	if err != nil {
+		t.Fatalf("CleanExpired failed: %v", err)
+	}
+
+	if count := negativeCacheTableRowCount(t, cache); count != 1 {
+		t.Errorf("negative_cache holds %d rows after CleanExpired, want 1", count)
+	}
+
+	if negativeCacheRowCount(t, cache, notExpiredPath) != 1 {
+		t.Error("the row that has not expired was removed")
+	}
+}
+
+// TestCleanExpiredRemovesMoreThanOneBatch stores one expired negative
+// cache row more than one batch holds and calls CleanExpired once: it
+// must remove them all, so it fails if CleanExpired stops after its
+// first batch.
+func TestCleanExpiredRemovesMoreThanOneBatch(t *testing.T) {
+	t.Parallel()
+
+	cache, err := NewCache(evictionTestDB(t), CacheConfig{StateDir: t.TempDir()})
+	if err != nil {
+		t.Fatalf("failed to create cache: %v", err)
+	}
+
+	insertExpiredNegativeCacheRows(t, cache, cleanExpiredBatchSize+1)
+
+	before := negativeCacheTableRowCount(t, cache)
+
+	err = cache.CleanExpired(t.Context())
+	if err != nil {
+		t.Fatalf("CleanExpired failed: %v", err)
+	}
+
+	after := negativeCacheTableRowCount(t, cache)
+
+	t.Logf("CleanExpired removed %d of %d expired rows, %d per batch",
+		before-after, before, cleanExpiredBatchSize)
+
+	if after != 0 {
+		t.Errorf("negative_cache holds %d rows after CleanExpired, want 0", after)
+	}
+}
+
+// TestCleanExpiredStopsOnceContextEnds runs CleanExpired with a context
+// that has already ended: it must return the context's error and delete
+// no row.
+func TestCleanExpiredStopsOnceContextEnds(t *testing.T) {
+	t.Parallel()
+
+	cache, err := NewCache(evictionTestDB(t), CacheConfig{StateDir: t.TempDir()})
+	if err != nil {
+		t.Fatalf("failed to create cache: %v", err)
+	}
+
+	insertExpiredNegativeCacheRows(t, cache, 1)
+
+	ctx, cancel := context.WithCancel(t.Context())
+	cancel()
+
+	err = cache.CleanExpired(ctx)
+	if !errors.Is(err, context.Canceled) {
+		t.Errorf("CleanExpired() error = %v, want context.Canceled", err)
+	}
+
+	if count := negativeCacheTableRowCount(t, cache); count != 1 {
+		t.Errorf("negative_cache holds %d rows, want the expired row kept", count)
+	}
+}
+
+// insertExpiredNegativeCacheRows inserts count negative_cache rows that
+// expired an hour ago, each for a different source path.
+func insertExpiredNegativeCacheRows(t *testing.T, cache *Cache, count int) {
+	t.Helper()
+
+	for i := range count {
+		_, err := cache.db.ExecContext(t.Context(), `
+			INSERT INTO negative_cache
+				(source_host, source_path, status_code, expires_at)
+			VALUES (?, ?, 404, datetime('now', '-1 hour'))
+		`, testHostExample, "/expired/"+strconv.Itoa(i)+".jpg")
+		if err != nil {
+			t.Fatalf("failed to insert an expired row: %v", err)
+		}
+	}
+}
+
+// negativeCacheTableRowCount returns how many rows negative_cache holds.
+func negativeCacheTableRowCount(tb testing.TB, cache *Cache) int {
+	tb.Helper()
+
+	var count int
+
+	err := cache.db.QueryRowContext(tb.Context(),
+		`SELECT COUNT(*) FROM negative_cache`,
+	).Scan(&count)
+	if err != nil {
+		tb.Fatalf("failed to count negative_cache rows: %v", err)
+	}
+
+	return count
+}
+
 func TestService_Get_ReturnsErrorForNegativeCachedURL(t *testing.T) {
 	t.Parallel()
 

internal/imgcache/service.go

@@ -9,6 +9,7 @@ import (
 	"log/slog"
 	"net/url"
 	"runtime/debug"
+	"strings"
 	"time"
 
 	"github.com/dustin/go-humanize"
@@ -128,26 +129,20 @@ func NewService(cfg *ServiceConfig) (*Service, error) {
 // ErrNegativeCached is returned when a URL is in the negative cache (recently failed).
 var ErrNegativeCached = errors.New("request is in negative cache (recently failed)")
 
+// ErrProcessingTimedOut is returned when processing an image stopped because
+// the downstream_timeout of the request doing it ended, to that request and to
+// every request that waited for its image.
+var ErrProcessingTimedOut = errors.New(
+	"image processing stopped at the deadline of the request doing it")
+
 // Get retrieves a processed image, fetching and processing if necessary.
+// While its source URL is in the negative cache, a cached variant is still
+// served and a variant not in the cache is still made from a cached source;
+// only a request that needs the source fetched is refused.
 func (s *Service) Get(ctx context.Context, req *ImageRequest) (*ImageResponse, error) {
 	// Propagate AllowHTTP setting to the request
 	req.AllowHTTP = s.allowHTTP
 
-	// Check negative cache first - skip fetching for recently-failed URLs
-	negHit, err := s.cache.checkNegativeCache(ctx, req)
-	if err != nil {
-		s.log.Warn("negative cache check failed", "error", err)
-	}
-
-	if negHit {
-		s.log.Debug("negative cache hit",
-			"host", req.SourceHost,
-			"path", req.SourcePath,
-		)
-
-		return nil, fmt.Errorf("%w: %w", httpfetcher.ErrUpstreamError, ErrNegativeCached)
-	}
-
 	// Check variant cache first (disk only, no DB)
 	result, err := s.cache.Lookup(ctx, req)
 	if err != nil {
@@ -218,7 +213,16 @@ func (s *Service) ValidateRequest(req *ImageRequest) error {
 		return fmt.Errorf("invalid source URL: %w", err)
 	}
 
-	if s.allowlist.IsAllowed(parsedURL) {
+	// An allowlist entry names no port, so a host followed by ":", with or
+	// without a port, needs a signature. The port is read from the parsed
+	// URL, as the fetcher reads it: in an IPv6 address written without
+	// brackets, such as 2001:db8::1:8443, it is what follows the last ":".
+	// This is checked here and not in allowlist.IsAllowed, which also matches
+	// referer_blocklist, where a Referer must be blocked whatever its port.
+	hostHasPort := parsedURL.Port() != "" ||
+		strings.HasSuffix(parsedURL.Host, ":")
+
+	if !hostHasPort && s.allowlist.IsAllowed(parsedURL) {
 		return nil
 	}
 
@@ -423,12 +427,28 @@ func (s *Service) processFromSourceOrFetch(
 
 // fetchAndProcess fetches from upstream, processes, and caches the result.
 // It counts the fetch with the bytes read from upstream, including when
-// reading the response or a later step fails.
+// reading the response or a later step fails. It fetches nothing while the
+// source URL is in the negative cache.
 func (s *Service) fetchAndProcess(
 	ctx context.Context,
 	req *ImageRequest,
 	cacheKey VariantKey,
 ) (*processedVariant, error) {
+	// Check negative cache - skip fetching for recently-failed URLs
+	negHit, err := s.cache.checkNegativeCache(ctx, req)
+	if err != nil {
+		s.log.Warn("negative cache check failed", "error", err)
+	}
+
+	if negHit {
+		s.log.Debug("negative cache hit",
+			"host", req.SourceHost,
+			"path", req.SourcePath,
+		)
+
+		return nil, fmt.Errorf("%w: %w", httpfetcher.ErrUpstreamError, ErrNegativeCached)
+	}
+
 	// Fetch from upstream
 	sourceURL := req.SourceURL()
 
@@ -535,7 +555,13 @@ func (s *Service) processAndStore(
 		FitMode: imageprocessor.FitMode(req.FitMode),
 	}
 
+	// ctx has the deadline of the request doing the processing, which can
+	// end while a request waiting for its image has time left
 	processResult, err := s.processor.Process(ctx, source, processReq)
+	if errors.Is(err, context.DeadlineExceeded) {
+		return nil, fmt.Errorf("%w: %w", ErrProcessingTimedOut, err)
+	}
+
 	if err != nil {
 		return nil, fmt.Errorf("image processing failed: %w", err)
 	}

internal/imgcache/service_internal_test.go

@@ -250,6 +250,97 @@ func TestService_ValidateRequest_SignatureExactHostMatch(t *testing.T) {
 	}
 }
 
+// TestService_ValidateRequest_HostWithPortNeedsSignature verifies that a host
+// followed by a port, or by a colon with no port, matches no allowlist entry,
+// so that a request for it without a signature is refused, while the same
+// host with no port is allowlisted.
+func TestService_ValidateRequest_HostWithPortNeedsSignature(t *testing.T) {
+	t.Parallel()
+
+	svc, _ := SetupTestService(t,
+		WithSigningKey(testSigningKey),
+		WithAllowlist(testHostCDN, "203.0.113.5", "2001:db8::1"),
+	)
+
+	tests := []struct {
+		host        string
+		allowlisted bool
+	}{
+		{testHostCDN, true},
+		{"cdn.example.com:8443", false},
+		{"cdn.example.com:443", false},
+		{"cdn.example.com:", false},
+		{"203.0.113.5", true},
+		{"203.0.113.5:8080", false},
+		{"[2001:db8::1]", true},
+		{"[2001:db8::1]:8443", false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.host, func(t *testing.T) {
+			t.Parallel()
+
+			req := &ImageRequest{
+				SourceHost: tt.host,
+				SourcePath: testPathCat,
+				Size:       Size{Width: 50, Height: 50},
+				Format:     FormatJPEG,
+				Quality:    85,
+				FitMode:    FitCover,
+			}
+
+			err := svc.ValidateRequest(req)
+			t.Logf("ValidateRequest() for host %q with no signature: %v",
+				tt.host, err)
+
+			if allowlisted := err == nil; allowlisted != tt.allowlisted {
+				t.Errorf("host %q served without a signature = %v, want %v",
+					tt.host, allowlisted, tt.allowlisted)
+			}
+		})
+	}
+}
+
+// TestService_ValidateRequest_UnbracketedIPv6PortNeedsSignature verifies that
+// an allowlisted IPv6 address written without brackets and followed by a
+// port, or by a colon with no port, needs a signature. Go's URL parser, which
+// the fetcher uses, reads 2001:db8::1:8443 as the host 2001:db8::1 with the
+// port 8443.
+func TestService_ValidateRequest_UnbracketedIPv6PortNeedsSignature(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	svc, _ := SetupTestService(t,
+		WithSigningKey(testSigningKey),
+		WithAllowlist("2001:db8::1"),
+	)
+
+	for _, host := range []string{"2001:db8::1:8443", "2001:db8::1:"} {
+		t.Run(host, func(t *testing.T) {
+			t.Parallel()
+
+			req := &ImageRequest{
+				SourceHost: host,
+				SourcePath: testPathCat,
+				Size:       Size{Width: 50, Height: 50},
+				Format:     FormatJPEG,
+				Quality:    85,
+				FitMode:    FitCover,
+			}
+
+			err := svc.ValidateRequest(req)
+			t.Logf("ValidateRequest() for host %q with no signature: %v",
+				host, err)
+
+			if err == nil {
+				t.Errorf("host %q served without a signature, want refused",
+					host)
+			}
+		})
+	}
+}
+
 func TestService_Get_InvalidFile(t *testing.T) {
 	t.Parallel()
 

internal/imgcache/urlparser.go

@@ -15,6 +15,7 @@ import (
 var (
 	ErrInvalidPath       = errors.New("invalid image path")
 	ErrMissingHost       = errors.New("missing source host")
+	ErrInvalidHost       = errors.New("invalid source host")
 	ErrMissingSize       = errors.New("missing size specification")
 	ErrInvalidSize       = errors.New("invalid size format")
 	ErrInvalidFormat     = errors.New("invalid or unsupported format")
@@ -143,6 +144,17 @@ func parseImageComponents(remainder string) (*ParsedURL, error) {
 		return nil, ErrMissingHost
 	}
 
+	// A URL reads what comes before "@" as a user name and password, and the
+	// rest as the host
+	if strings.Contains(host, "@") {
+		return nil, fmt.Errorf("%w: %q holds @", ErrInvalidHost, host)
+	}
+
+	// Host names do not depend on letter case, so the allowlist, the upstream
+	// connection limits, the cache and the signature see one spelling of each
+	// host
+	host = strings.ToLower(host)
+
 	// Extract query string if present in path
 	if qIndex := strings.Index(path, "?"); qIndex != -1 {
 		query = path[qIndex+1:]

internal/imgcache/urlparser_internal_test.go

@@ -234,6 +234,49 @@ func TestParseImagePath(t *testing.T) {
 	}
 }
 
+// TestParseImagePath_LowerCasesHost verifies that the host is lower-cased, so
+// that every spelling of its letter case is the same host to the allowlist,
+// the upstream connection limits and the cache, and that the path keeps its
+// case.
+func TestParseImagePath_LowerCasesHost(t *testing.T) {
+	t.Parallel()
+
+	got, err := ParseImagePath("CDN.Example.COM/Photos/Cat.jpg/800x600.webp")
+	if err != nil {
+		t.Fatalf("ParseImagePath() error = %v", err)
+	}
+
+	t.Logf("parsed host %q, path %q", got.Host, got.Path)
+
+	if got.Host != testHostCDN {
+		t.Errorf("Host = %q, want %q", got.Host, testHostCDN)
+	}
+
+	if got.Path != "/Photos/Cat.jpg" {
+		t.Errorf("Path = %q, want %q", got.Path, "/Photos/Cat.jpg")
+	}
+}
+
+// TestParseImagePath_RefusesUserinfo verifies that a host holding "@" is
+// refused: a URL reads what comes before the "@" as a user name and password
+// and the rest as the host.
+func TestParseImagePath_RefusesUserinfo(t *testing.T) {
+	t.Parallel()
+
+	for _, input := range []string{
+		"user@cdn.example.com/photos/cat.jpg/800x600.webp",
+		"user:password@cdn.example.com/photos/cat.jpg/800x600.webp",
+	} {
+		got, err := ParseImagePath(input)
+		t.Logf("ParseImagePath(%q) = %+v, error = %v", input, got, err)
+
+		if !errors.Is(err, ErrInvalidHost) {
+			t.Errorf("ParseImagePath(%q) error = %v, want %v",
+				input, err, ErrInvalidHost)
+		}
+	}
+}
+
 func TestParsedURL_ToImageRequest(t *testing.T) {
 	t.Parallel()