diff --git a/server/internal/cli/client.go b/server/internal/cli/client.go
index 349bfbcbd..fd39acf2e 100644
--- a/server/internal/cli/client.go
+++ b/server/internal/cli/client.go
@@ -326,11 +326,28 @@ func (c *APIClient) UploadFile(ctx context.Context, fileData []byte, filename st
 // DownloadFile downloads a file from the given URL and returns the response body.
 // This is used for downloading attachments via their signed download_url.
 // Downloads are limited to 100 MB to match the upload size limit.
+//
+// The URL may be absolute (a signed CloudFront/S3 URL) or relative
+// (a server-relative path like "/uploads/...") depending on how the
+// server is configured. Relative URLs are resolved against the client's
+// BaseURL and sent with the standard auth headers; absolute URLs are
+// used as-is so that their query-string signatures are not disturbed.
 func (c *APIClient) DownloadFile(ctx context.Context, downloadURL string) ([]byte, error) {
+	isRelative := !strings.HasPrefix(downloadURL, "http://") && !strings.HasPrefix(downloadURL, "https://")
+	if isRelative {
+		if c.BaseURL == "" {
+			return nil, fmt.Errorf("download URL %q is relative but client has no BaseURL", downloadURL)
+		}
+		downloadURL = c.BaseURL + downloadURL
+	}
+
 	req, err := http.NewRequestWithContext(ctx, http.MethodGet, downloadURL, nil)
 	if err != nil {
 		return nil, err
 	}
+	if isRelative {
+		c.setHeaders(req)
+	}
 
 	resp, err := c.HTTPClient.Do(req)
 	if err != nil {
diff --git a/server/internal/cli/client_test.go b/server/internal/cli/client_test.go
index c49276f0d..6248f4455 100644
--- a/server/internal/cli/client_test.go
+++ b/server/internal/cli/client_test.go
@@ -164,6 +164,76 @@ func TestPostJSON(t *testing.T) {
 	})
 }
 
+func TestDownloadFile(t *testing.T) {
+	t.Run("relative URL is resolved against BaseURL and sent with auth", func(t *testing.T) {
+		var gotPath, gotAuth string
+		srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			gotPath = r.URL.Path
+			gotAuth = r.Header.Get("Authorization")
+			w.Write([]byte("hello"))
+		}))
+		defer srv.Close()
+
+		client := NewAPIClient(srv.URL, "", "test-token")
+		data, err := client.DownloadFile(context.Background(), "/uploads/workspaces/abc/file.md")
+		if err != nil {
+			t.Fatalf("unexpected error: %v", err)
+		}
+		if string(data) != "hello" {
+			t.Errorf("unexpected body: %q", string(data))
+		}
+		if gotPath != "/uploads/workspaces/abc/file.md" {
+			t.Errorf("unexpected path: %q", gotPath)
+		}
+		if gotAuth != "Bearer test-token" {
+			t.Errorf("expected Authorization Bearer test-token, got %q", gotAuth)
+		}
+	})
+
+	t.Run("absolute URL is used as-is without auth headers", func(t *testing.T) {
+		var gotAuth string
+		srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			gotAuth = r.Header.Get("Authorization")
+			w.Write([]byte("signed-payload"))
+		}))
+		defer srv.Close()
+
+		client := NewAPIClient("https://api.example.test", "", "test-token")
+		data, err := client.DownloadFile(context.Background(), srv.URL+"/signed?sig=abc")
+		if err != nil {
+			t.Fatalf("unexpected error: %v", err)
+		}
+		if string(data) != "signed-payload" {
+			t.Errorf("unexpected body: %q", string(data))
+		}
+		if gotAuth != "" {
+			t.Errorf("expected no Authorization header on signed URL, got %q", gotAuth)
+		}
+	})
+
+	t.Run("relative URL with empty BaseURL returns a helpful error", func(t *testing.T) {
+		client := NewAPIClient("", "", "test-token")
+		_, err := client.DownloadFile(context.Background(), "/uploads/x.md")
+		if err == nil {
+			t.Fatal("expected error, got nil")
+		}
+	})
+
+	t.Run("non-2xx status returns an error with the response body", func(t *testing.T) {
+		srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			w.WriteHeader(http.StatusNotFound)
+			io.WriteString(w, "not found")
+		}))
+		defer srv.Close()
+
+		client := NewAPIClient(srv.URL, "", "test-token")
+		_, err := client.DownloadFile(context.Background(), "/uploads/missing")
+		if err == nil {
+			t.Fatal("expected error, got nil")
+		}
+	})
+}
+
 func TestNormalizeGOOS(t *testing.T) {
 	cases := map[string]string{
 		"darwin":  "macos",