When exporting to Texinfo, the patch below makes it easier to generate
a good `@direntry` by using sane defaults.
For most files, you'll just need

    #+TEXINFO_DIR_CATEGORY: {my-category}

I believe it also makes it a bit harder to shoot oneself in the foot and
generate an invalid entry (e.g. with a missing or wrong file name).


        Stefan
diff --git a/lisp/org/ox-texinfo.el b/lisp/org/ox-texinfo.el
index 84313645e6e..beea7aacab7 100644
--- a/lisp/org/ox-texinfo.el
+++ b/lisp/org/ox-texinfo.el
@@ -817,17 +799,27 @@ org-texinfo-template
 		   (org-export-data copying info))))
      ;; Info directory information.  Only supply if both title and
      ;; category are provided.
-     (let ((dircat (plist-get info :texinfo-dircat))
-	   (dirtitle
-	    (let ((title (plist-get info :texinfo-dirtitle)))
-	      (and title
-		   (string-match "^\\(?:\\* \\)?\\(.*?\\)\\(\\.\\)?$" title)
-		   (format "* %s." (match-string 1 title))))))
-       (when (and dircat dirtitle)
+     (let* ((dircat (plist-get info :texinfo-dircat))
+	    (dt (plist-get info :texinfo-dirtitle))
+	    (file (file-name-sans-extension
+		   (or (org-strip-quotes (plist-get info :texinfo-filename))
+		       (plist-get info :output-file))))
+	    (dirtitle
+             (cond
+              ((and dt
+                    (or (string-match "\\`\\* \\(.*?\\)\\(\\.\\)?\\'" dt)
+                        (string-match "\\`\\(.*(.*)\\)\\(\\.\\)?\\'" dt)))
+               ;; `dt' is already "complete".
+               (format "* %s." (match-string 1 dt)))
+              ((and dt (not (equal dt file)))
+               (format "* %s: (%s)." dt file))
+              (t (format "* %s." file)))))
+       (when dircat
 	 (concat "@dircategory " dircat "\n"
 		 "@direntry\n"
 		 (let ((dirdesc
-			(let ((desc (plist-get info :texinfo-dirdesc)))
+			(let ((desc (or (plist-get info :texinfo-dirdesc)
+			                title)))
 			  (cond ((not desc) nil)
 				((string-suffix-p "." desc) desc)
 				(t (concat desc "."))))))
@@ -1590,7 +1582,7 @@ org-texinfo-planning
   (concat
    "@noindent"
    (mapconcat
-    'identity
+    #'identity
     (delq nil
 	  (list
 	   (let ((closed (org-element-property :closed planning)))

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