diff --git a/cmd/gateway.go b/cmd/gateway.go
index 610e14cb..7ecd98c6 100644
--- a/cmd/gateway.go
+++ b/cmd/gateway.go
@@ -386,7 +386,7 @@ func runGateway() {
 
 	// Workspace file serving endpoint — serves files by absolute path, auth-token protected.
 	// Supports media from any agent workspace (each agent has its own workspace from DB).
-	server.SetFilesHandler(httpapi.NewFilesHandler(cfg.Gateway.Token))
+	server.SetFilesHandler(httpapi.NewFilesHandler(cfg.Gateway.Token, workspace))
 
 	// Storage file management — browse/delete files under the resolved workspace directory.
 	// Uses GOCLAW_WORKSPACE (or default ~/.goclaw/workspace) so it works correctly
diff --git a/internal/http/files.go b/internal/http/files.go
index bd439c75..fb4ea872 100644
--- a/internal/http/files.go
+++ b/internal/http/files.go
@@ -13,13 +13,17 @@ import (
 
 // FilesHandler serves files over HTTP with Bearer token auth.
 // Accepts absolute paths — the auth token protects against unauthorized access.
+// When an exact path is not found, falls back to searching the workspace for
+// generated files by basename (goclaw_gen_* filenames are globally unique).
 type FilesHandler struct {
-	token string
+	token     string
+	workspace string // workspace root for fallback file search
 }
 
 // NewFilesHandler creates a handler that serves files by absolute path.
-func NewFilesHandler(token string) *FilesHandler {
-	return &FilesHandler{token: token}
+// workspace is the root directory used for fallback generated file search.
+func NewFilesHandler(token, workspace string) *FilesHandler {
+	return &FilesHandler{token: token, workspace: workspace}
 }
 
 // RegisterRoutes registers the file serving route.
@@ -79,8 +83,15 @@ func (h *FilesHandler) handleServe(w http.ResponseWriter, r *http.Request) {
 
 	info, err := os.Stat(absPath)
 	if err != nil || info.IsDir() {
-		http.NotFound(w, r)
-		return
+		// Fallback: search workspace for file by basename (handles LLM-hallucinated paths).
+		// Generated filenames (goclaw_gen_*) include nanosecond timestamps and are globally unique.
+		if resolved := h.findInWorkspace(filepath.Base(absPath)); resolved != "" {
+			absPath = resolved
+			info, _ = os.Stat(absPath)
+		} else {
+			http.NotFound(w, r)
+			return
+		}
 	}
 
 	// Set Content-Type from extension
@@ -92,3 +103,49 @@ func (h *FilesHandler) handleServe(w http.ResponseWriter, r *http.Request) {
 
 	http.ServeFile(w, r, absPath)
 }
+
+// findInWorkspace searches the workspace directory tree for a file by basename.
+// Returns the absolute path if found, empty string otherwise.
+// Only searches under "generated/" subdirectories to limit scope.
+func (h *FilesHandler) findInWorkspace(basename string) string {
+	if h.workspace == "" || basename == "" {
+		return ""
+	}
+	var found string
+	_ = filepath.WalkDir(h.workspace, func(path string, d os.DirEntry, err error) error {
+		if err != nil {
+			return filepath.SkipDir
+		}
+		if d.IsDir() {
+			// Only descend into "generated" directories (and their parents).
+			name := d.Name()
+			if name == "generated" || name == "teams" || name == h.workspace {
+				return nil
+			}
+			// Allow date directories under generated/ (e.g. 2026-03-20)
+			if len(name) == 10 && name[4] == '-' {
+				return nil
+			}
+			// Allow team/user ID directories
+			if strings.Contains(name, "-") || isNumeric(name) {
+				return nil
+			}
+			return filepath.SkipDir
+		}
+		if d.Name() == basename {
+			found = path
+			return filepath.SkipAll
+		}
+		return nil
+	})
+	return found
+}
+
+func isNumeric(s string) bool {
+	for _, c := range s {
+		if c < '0' || c > '9' {
+			return false
+		}
+	}
+	return len(s) > 0
+}
diff --git a/ui/web/src/components/shared/markdown-renderer.tsx b/ui/web/src/components/shared/markdown-renderer.tsx
index 6c9e4b37..54ce9ffe 100644
--- a/ui/web/src/components/shared/markdown-renderer.tsx
+++ b/ui/web/src/components/shared/markdown-renderer.tsx
@@ -63,15 +63,18 @@ function isFileLink(href: string | undefined): boolean {
   return false;
 }
 
-/** Convert a local file path to a /v1/files/ URL for serving */
+/** Convert a local file path to a /v1/files/ URL for serving.
+ *  For relative paths, uses just the filename so the backend fallback search
+ *  can find generated files regardless of the directory the LLM wrote. */
 function toFileUrl(href: string, token?: string): string {
   let url: string;
   if (href.startsWith("/v1/files/") || href.includes("/v1/files/")) {
     url = href;
   } else {
-    // For relative paths, strip leading ./ or ../ and route through /v1/files/
-    const cleaned = href.replace(/^\.\.?\//, "");
-    url = `/v1/files/${cleaned}`;
+    // For relative paths, use just the basename — the backend will search
+    // the workspace for the file by name (goclaw_gen_* names are unique).
+    const basename = href.split("/").pop() ?? href;
+    url = `/v1/files/${basename}`;
   }
   // Append auth token as query param (server accepts ?token= for file serving)
   if (token) {