diff --git a/internal/web/uploads_logging_handler_test.go b/internal/web/uploads_logging_handler_test.go
new file mode 100644
index 0000000..e29a33e
--- /dev/null
+++ b/internal/web/uploads_logging_handler_test.go
@@ -0,0 +1,72 @@
+package web_test
+
+import (
+	"bytes"
+	"context"
+	"errors"
+	"io"
+	"log/slog"
+	"net/http"
+	"net/url"
+	"sync"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// Error paths of the upload routes log a kind, never the error's text, which can carry
+// a file name, a path, a database value or a provider's output (adversarial review F5).
+
+type lockedBuf struct {
+	mu sync.Mutex
+	b  bytes.Buffer
+}
+
+func (l *lockedBuf) Write(p []byte) (int, error) {
+	l.mu.Lock()
+	defer l.mu.Unlock()
+	return l.b.Write(p)
+}
+
+func (l *lockedBuf) String() string {
+	l.mu.Lock()
+	defer l.mu.Unlock()
+	return l.b.String()
+}
+
+type failingUploader struct{ err error }
+
+func (f failingUploader) Accept(context.Context, string, string, io.Reader) (string, error) {
+	return "", f.err
+}
+
+func TestUploadPost_AnUnexpectedFailureLogsAKindAndNotItsText(t *testing.T) {
+	app, _ := newUploadApp(t, audioOK, 200<<20)
+	buf := &lockedBuf{}
+	app.Log = slog.New(slog.NewTextHandler(buf, nil))
+	app.Uploads = failingUploader{err: errors.New(`ffprobe: Error opening input file /spool/upload-555 for "zebrakaka-meeting.m4a"`)}
+
+	rec := do(t, app, uploadReq(t, "t", "zebrakaka-meeting.m4a", []byte("x")))
+
+	assert.Equal(t, http.StatusInternalServerError, rec.Code)
+	out := buf.String()
+	assert.NotContains(t, out, "zebrakaka", "a file name is private content")
+	assert.NotContains(t, out, "/spool/", "a spool path carries the upload's identity")
+	assert.Contains(t, out, "kind=error")
+}
+
+func TestUploadChatPost_AModelFailureLogsAKindAndNotItsText(t *testing.T) {
+	app, fc := newUploadChatApp(t)
+	buf := &lockedBuf{}
+	app.Log = slog.New(slog.NewTextHandler(buf, nil))
+	fc.err = errors.New("LLM returned 400: the prompt was zebrakaka secret words")
+	id := seedUpload(t, userID, "m", "done", meetingText)
+
+	rec := do(t, app, chatPost("/uploads/"+id+"/chat", url.Values{"question": {"q"}}))
+
+	require.Equal(t, http.StatusOK, rec.Code)
+	out := buf.String()
+	assert.NotContains(t, out, "zebrakaka")
+	assert.Contains(t, out, "kind=error")
+}