python · bitdancer · Feb 24, 2026 · Feb 19, 2026
@@ -80,7 +80,8 @@
 # Useful constants and functions
 #
 
-WSP = set(' \t')
+_WSP = ' \t'
+WSP = set(_WSP)
 CFWS_LEADER = WSP | set('(')
 SPECIALS = set(r'()<>@,:;.\"[]')
 ATOM_ENDS = SPECIALS | WSP
@@ -2831,6 +2832,7 @@ def _steal_trailing_WSP_if_exists(lines):
             lines.pop()
     return wsp
 
+
 def _refold_parse_tree(parse_tree, *, policy):
     """Return string of contents of parse_tree folded according to RFC rules.
 
@@ -2839,11 +2841,9 @@ def _refold_parse_tree(parse_tree, *, policy):
     maxlen = policy.max_line_length or sys.maxsize
     encoding = 'utf-8' if policy.utf8 else 'us-ascii'
     lines = ['']  # Folded lines to be output
-    leading_whitespace = ''  # When we have whitespace between two encoded
-                             # words, we may need to encode the whitespace
-                             # at the beginning of the second word.
-    last_ew = None  # Points to the last encoded character if there's an ew on
-                    # the line
+    last_word_is_ew = False
+    last_ew = None  # if there is an encoded word in the last line of lines,
+                    # points to the encoded word's first character
     last_charset = None
     wrap_as_ew_blocked = 0
     want_encoding = False  # This is set to True if we need to encode this part
@@ -2878,6 +2878,7 @@ def _refold_parse_tree(parse_tree, *, policy):
         if part.token_type == 'mime-parameters':
             # Mime parameter folding (using RFC2231) is extra special.
             _fold_mime_parameters(part, lines, maxlen, encoding)
+            last_word_is_ew = False
             continue
 
         if want_encoding and not wrap_as_ew_blocked:
@@ -2894,6 +2895,7 @@ def _refold_parse_tree(parse_tree, *, policy):
                             # XXX what if encoded_part has no leading FWS?
                             lines.append(newline)
                         lines[-1] += encoded_part
+                        last_word_is_ew = False
                         continue
                 # Either this is not a major syntactic break, so we don't
                 # want it on a line by itself even if it fits, or it
@@ -2912,11 +2914,16 @@ def _refold_parse_tree(parse_tree, *, policy):
                     (last_charset == 'unknown-8bit' or
                      last_charset == 'utf-8' and charset != 'us-ascii')):
                     last_ew = None
-                last_ew = _fold_as_ew(tstr, lines, maxlen, last_ew,
-                                      part.ew_combine_allowed, charset, leading_whitespace)
-                # This whitespace has been added to the lines in _fold_as_ew()
-                # so clear it now.
-                leading_whitespace = ''
+                last_ew = _fold_as_ew(
+                    tstr,
+                    lines,
+                    maxlen,
+                    last_ew,
+                    part.ew_combine_allowed,
+                    charset,
+                    last_word_is_ew,
+                )
+                last_word_is_ew = True
                 last_charset = charset
                 want_encoding = False
                 continue
@@ -2929,28 +2936,19 @@ def _refold_parse_tree(parse_tree, *, policy):
 
         if len(tstr) <= maxlen - len(lines[-1]):
             lines[-1] += tstr
+            last_word_is_ew = last_word_is_ew and not bool(tstr.strip(_WSP))
             continue
 
         # This part is too long to fit.  The RFC wants us to break at
         # "major syntactic breaks", so unless we don't consider this
         # to be one, check if it will fit on the next line by itself.
-        leading_whitespace = ''
         if (part.syntactic_break and
                 len(tstr) + 1 <= maxlen):
             newline = _steal_trailing_WSP_if_exists(lines)
             if newline or part.startswith_fws():
-                # We're going to fold the data onto a new line here.  Due to
-                # the way encoded strings handle continuation lines, we need to
-                # be prepared to encode any whitespace if the next line turns
-                # out to start with an encoded word.
                 lines.append(newline + tstr)
-
-                whitespace_accumulator = []
-                for char in lines[-1]:
-                    if char not in WSP:
-                        break
-                    whitespace_accumulator.append(char)
-                leading_whitespace = ''.join(whitespace_accumulator)
+                last_word_is_ew = (last_word_is_ew
+                                   and not bool(lines[-1].strip(_WSP)))
                 last_ew = None
                 continue
         if not hasattr(part, 'encode'):
@@ -2990,10 +2988,11 @@ def _refold_parse_tree(parse_tree, *, policy):
         else:
             # We can't fold it onto the next line either...
             lines[-1] += tstr
+        last_word_is_ew = last_word_is_ew and not bool(tstr.strip(_WSP))
 
     return policy.linesep.join(lines) + policy.linesep
 
-def _fold_as_ew(to_encode, lines, maxlen, last_ew, ew_combine_allowed, charset, leading_whitespace):
+def _fold_as_ew(to_encode, lines, maxlen, last_ew, ew_combine_allowed, charset, last_word_is_ew):
     """Fold string to_encode into lines as encoded word, combining if allowed.
     Return the new value for last_ew, or None if ew_combine_allowed is False.
 
@@ -3008,6 +3007,16 @@ def _fold_as_ew(to_encode, lines, maxlen, last_ew, ew_combine_allowed, charset,
         to_encode = str(
             get_unstructured(lines[-1][last_ew:] + to_encode))
         lines[-1] = lines[-1][:last_ew]
+    elif last_word_is_ew:
+        # If we are following up an encoded word with another encoded word,
+        # any white space between the two will be ignored when decoded.
+        # Therefore, we encode all to-be-displayed whitespace in the second
+        # encoded word.
+        len_without_wsp = len(lines[-1].rstrip(_WSP))
+        leading_whitespace = lines[-1][len_without_wsp:]
+        lines[-1] = (lines[-1][:len_without_wsp]
+                     + (' ' if leading_whitespace else ''))
+        to_encode = leading_whitespace + to_encode
     elif to_encode[0] in WSP:
         # We're joining this to non-encoded text, so don't encode
         # the leading blank.
@@ -3036,20 +3045,13 @@ def _fold_as_ew(to_encode, lines, maxlen, last_ew, ew_combine_allowed, charset,
 
     while to_encode:
         remaining_space = maxlen - len(lines[-1])
-        text_space = remaining_space - chrome_len - len(leading_whitespace)
+        text_space = remaining_space - chrome_len
         if text_space <= 0:
-            lines.append(' ')
+            newline = _steal_trailing_WSP_if_exists(lines)
+            lines.append(newline or ' ')
+            new_last_ew = len(lines[-1])
             continue
 
-        # If we are at the start of a continuation line, prepend whitespace
-        # (we only want to do this when the line starts with an encoded word
-        # but if we're folding in this helper function, then we know that we
-        # are going to be writing out an encoded word.)
-        if len(lines) > 1 and len(lines[-1]) == 1 and leading_whitespace:
-            encoded_word = _ew.encode(leading_whitespace, charset=encode_as)
-            lines[-1] += encoded_word
-            leading_whitespace = ''
-
         to_encode_word = to_encode[:text_space]
         encoded_word = _ew.encode(to_encode_word, charset=encode_as)
         excess = len(encoded_word) - remaining_space
@@ -3061,7 +3063,6 @@ def _fold_as_ew(to_encode, lines, maxlen, last_ew, ew_combine_allowed, charset,
             excess = len(encoded_word) - remaining_space
         lines[-1] += encoded_word
         to_encode = to_encode[len(to_encode_word):]
-        leading_whitespace = ''
 
         if to_encode:
             lines.append(' ')

@@ -393,6 +393,50 @@ def test_defaults_handle_spaces_at_start_of_continuation_line(self):
         g.flatten(msg)
         self.assertEqual(s.getvalue(), expected)
 
+    # gh-144156: fold between non-encoded and encoded words don't need to encoded
+    #            the separating space
+    def test_defaults_handle_spaces_at_start_of_continuation_line_2(self):
+        source = ("Re: [SOS-1495488] Commande et livraison - Demande de retour - "
+                  "bibijolie - 251210-AABBCC - Abo actualités digitales 20 semaines "
+                  "d’abonnement à 24 heures, Bilan, Tribune de Genève et tous les titres Tamedia")
+        expected = (
+            b"Subject: "
+            b"Re: [SOS-1495488] Commande et livraison - Demande de retour -\n"
+            b" bibijolie - 251210-AABBCC - Abo =?utf-8?q?actualit=C3=A9s?= digitales 20\n"
+            b" semaines =?utf-8?q?d=E2=80=99abonnement_=C3=A0?= 24 heures, Bilan, Tribune de\n"
+            b" =?utf-8?q?Gen=C3=A8ve?= et tous les titres Tamedia\n\n"
+        )
+        msg = EmailMessage()
+        msg['Subject'] = source
+        s = io.BytesIO()
+        g = BytesGenerator(s)
+        g.flatten(msg)
+        self.assertEqual(s.getvalue(), expected)
+
+    def test_ew_folding_round_trip_1(self):
+        print()
+        source = "aaaaaaaaa фффффффф "
+        msg = EmailMessage()
+        msg['Subject'] = source
+        s = io.BytesIO()
+        g = BytesGenerator(s, maxheaderlen=30)
+        g.flatten(msg)
+        flat = s.getvalue()
+        reparsed = message_from_bytes(flat, policy=policy.default)['Subject']
+        self.assertMultiLineEqual(reparsed, source)
+
+    def test_ew_folding_round_trip_2(self):
+        print()
+        source = "aaa aaaaaaa   aaa ффф фффф  "
+        msg = EmailMessage()
+        msg['Subject'] = source
+        s = io.BytesIO()
+        g = BytesGenerator(s, maxheaderlen=30)
+        g.flatten(msg)
+        flat = s.getvalue()
+        reparsed = message_from_bytes(flat, policy=policy.default)['Subject']
+        self.assertMultiLineEqual(reparsed, source)
+
     def test_cte_type_7bit_handles_unknown_8bit(self):
         source = ("Subject: Maintenant je vous présente mon "
                  "collègue\n\n").encode('utf-8')

@@ -1703,7 +1703,7 @@ def test_fold_unstructured_with_overlong_word(self):
             'singlewordthatwontfit')
         self.assertEqual(
             h.fold(policy=policy.default.clone(max_line_length=20)),
-            'Subject: \n'
+            'Subject:\n'
             ' =?utf-8?q?thisisa?=\n'
             ' =?utf-8?q?verylon?=\n'
             ' =?utf-8?q?glineco?=\n'
@@ -1719,7 +1719,7 @@ def test_fold_unstructured_with_two_overlong_words(self):
             'singlewordthatwontfit plusanotherverylongwordthatwontfit')
         self.assertEqual(
             h.fold(policy=policy.default.clone(max_line_length=20)),
-            'Subject: \n'
+            'Subject:\n'
             ' =?utf-8?q?thisisa?=\n'
             ' =?utf-8?q?verylon?=\n'
             ' =?utf-8?q?glineco?=\n'

@@ -273,7 +273,7 @@ def test_non_ascii_chars_do_not_cause_inf_loop(self):
         actual = policy.fold('Subject', 'ą' * 12)
         self.assertEqual(
             actual,
-            'Subject: \n' +
+            'Subject:\n' +
             12 * ' =?utf-8?q?=C4=85?=\n')
 
     def test_short_maxlen_error(self):

diff --git a/Misc/NEWS.d/next/Library/2026-02-10-22-05-51.gh-issue-144156.UbrC7F.rst b/Misc/NEWS.d/next/Library/2026-02-10-22-05-51.gh-issue-144156.UbrC7F.rst
@@ -0,0 +1 @@
+Fix the folding of headers by the :mod:`email` library when :rfc:`2047` encoded words are used.  Now whitespace is correctly preserved and also correctly added between adjacent encoded words.  The latter property was broken by the fix for gh-92081, which mostly fixed previous failures to preserve whitespace.
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1 @@
		Fix the folding of headers by the :mod:`email` library when :rfc:`2047` encoded words are used. Now whitespace is correctly preserved and also correctly added between adjacent encoded words. The latter property was broken by the fix for gh-92081, which mostly fixed previous failures to preserve whitespace.