Hi,

Axel Svensson writes:
Steps to reproduce:
1) In an empty org-mode buffer, type a * SPC a C-b C-b C-b <RET>.
2) The buffer now has two lines, the first one "a" and the second "* a".

Expected:
3) The second line is formatted as a first-level heading.

Actual:
3) The second line is formatted as normal text.

Thanks for the report, I can confirm this bug with latest org.

Here's a patch that fixes this.

Regards,

--
Sébastien Miquel

>From c598f705bf1d8003514751fffc07fd64620a7e42 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?S=C3=A9bastien=20Miquel?= <sebastien.miq...@posteo.eu>
Date: Fri, 28 May 2021 21:14:22 +0200
Subject: [PATCH] org.el (org-fontify-extend-region): Fix headline
 fontification in edge case

* lisp/org.el (org-fontify-extend-region): Fix fontification of
headline or meta line created by inserting a newline.

Unrelated to the fix: `org-fontify-extend-region' is added to
`font-lock-extend-after-change-region-function' and doesn't need to
use `save-excursion'.
---
 lisp/org.el | 19 ++++++++++---------
 1 file changed, 10 insertions(+), 9 deletions(-)

diff --git a/lisp/org.el b/lisp/org.el
index 1bd9e02eb..b7b1416bd 100644
--- a/lisp/org.el
+++ b/lisp/org.el
@@ -5427,7 +5427,9 @@ by a #."
 	  t)))))

 (defun org-fontify-extend-region (beg end _old-len)
-  (let ((begin-re "\\(\\\\\\[\\|\\(#\\+begin_\\|\\\\begin{\\)\\S-+\\)")
+  (let ((end (if (progn (goto-char end) (looking-at-p "^[*#]"))
+                 (1+ end) end))
+        (begin-re "\\(\\\\\\[\\|\\(#\\+begin_\\|\\\\begin{\\)\\S-+\\)")
 	(end-re "\\(\\\\\\]\\|\\(#\\+end_\\|\\\\end{\\)\\S-+\\)")
 	(extend
          (lambda (r1 r2 dir)
@@ -5437,15 +5439,14 @@ by a #."
                        "[][]" r2
 		       (match-string-no-properties 0)))))
 	     (re-search-forward (regexp-quote re) nil t dir)))))
+    (goto-char beg)
+    (back-to-indentation)
     (save-match-data
-      (save-excursion
-	(goto-char beg)
-	(back-to-indentation)
-	(cond ((looking-at end-re)
-	       (cons (or (funcall extend "begin" "[" -1) beg) end))
-	      ((looking-at begin-re)
-	       (cons beg (or (funcall extend "end" "]" 1) end)))
-	      (t (cons beg end)))))))
+      (cond ((looking-at end-re)
+	     (cons (or (funcall extend "begin" "[" -1) beg) end))
+	    ((looking-at begin-re)
+	     (cons beg (or (funcall extend "end" "]" 1) end)))
+	    (t (cons beg end))))))

 (defun org-activate-footnote-links (limit)
   "Add text properties for footnotes."
-- 
2.31.1

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