diff --git a/docs/changelog/1214.bugfix.rst b/docs/changelog/1214.bugfix.rst
new file mode 100644
index 000000000..91c7640b9
--- /dev/null
+++ b/docs/changelog/1214.bugfix.rst
@@ -0,0 +1,2 @@
+``to_markdown`` keeps block content inside a heading on the heading line and reads a block edge in link text or a
+heading as a space.
diff --git a/src/turbohtml/_c/serialize/markdown.c b/src/turbohtml/_c/serialize/markdown.c
index 1233d23ed..b5d10dfee 100644
--- a/src/turbohtml/_c/serialize/markdown.c
+++ b/src/turbohtml/_c/serialize/markdown.c
@@ -163,6 +163,7 @@ enum md_leave {
     MD_LEAVE_TABLE,
     MD_LEAVE_BLOCKQUOTE, /* mark a quote that opened no block of its own */
     MD_LEAVE_BLOCK_END,  /* the block inside an inline element is done */
+    MD_LEAVE_SPACE,      /* a flattened block's end reads as a space */
 };
 
 enum md_table_phase {
@@ -1751,7 +1752,7 @@ static void md_render_inline_tag(md_ctx *ctx, th_node *node) {
         return;
     }
     if (is_md_block(atom)) {
-        if (!ctx->inline_only) {
+        if (!ctx->inline_only && !ctx->in_heading) {
             if (!ctx->in_cell) {
                 /* the content after the block belongs to a new block, so note where it ends;
                    a cell flattens its blocks onto its one line instead */
@@ -1765,10 +1766,13 @@ static void md_render_inline_tag(md_ctx *ctx, th_node *node) {
             md_enter_cell_flat(ctx, node, -1);
             return;
         }
-        /* inside link text a block cannot open its own line (a blank line would
-           split the CommonMark link), so it flattens to inline; its boundary still
-           reads as a space so adjacent words never fuse */
+        /* inside link text or a heading a block cannot open its own line (a blank
+           line would split the CommonMark link, and a heading is one line), so it
+           flattens to inline; its boundary still reads as a space so adjacent words
+           never fuse */
         ctx->space_pending = 1;
+        md_push(ctx, node, MD_WALK_INLINE, MD_LEAVE_SPACE);
+        return;
     }
     md_push(ctx, node, MD_WALK_INLINE, MD_LEAVE_NONE);
 }
@@ -3223,6 +3227,9 @@ static void md_leave(md_ctx *ctx) {
     case MD_LEAVE_BLOCK_END:
         ctx->block_ended = 1;
         break;
+    case MD_LEAVE_SPACE:
+        ctx->space_pending = 1;
+        break;
     case MD_LEAVE_BLOCKQUOTE:
         /* a leading quote writes its marker only with its first block; CommonMark
            reads a lone ">" as an empty quote, so keep one when no block came */
diff --git a/tests/serialize/test_markdown.py b/tests/serialize/test_markdown.py
index 32767e4d9..5c8e0975b 100644
--- a/tests/serialize/test_markdown.py
+++ b/tests/serialize/test_markdown.py
@@ -62,15 +62,23 @@ def md(html: str) -> str:
         pytest.param("<h3>a<br></h3>", "### a", id="heading-trailing-break-dropped"),
         pytest.param(
             "<h1><div><h2>x<br>y</h2>z<br>w</div></h1>",
-            "# \n\n## x y\n\nz w",
+            "# x y z w",
             id="nested-heading-keeps-break-as-space",
         ),
+        pytest.param("<h3><p>x</p></h3>", "### x", id="heading-paragraph-stays-in-heading"),
+        pytest.param("<h2>a<p>b</p>c</h2>", "## a b c", id="heading-block-edges-read-as-spaces"),
+        pytest.param("<h2><div>a</div><div>b</div></h2>", "## a b", id="heading-sibling-blocks-join"),
     ],
 )
 def test_headings(html: str, expected: str) -> None:
     assert md(html) == expected
 
 
+def test_setext_heading_keeps_block_content() -> None:
+    config: Final = Markdown(headings=Markdown.Headings(style="setext"))
+    assert parse_fragment("<h1>a<p>b</p></h1>").to_markdown(config) == "a b\n==="
+
+
 @pytest.mark.parametrize(
     ("html", "expected"),
     [
@@ -272,7 +280,7 @@ def test_code(html: str, expected: str) -> None:
             id="emphasis-adjacent-in-mtext-html",
         ),
         pytest.param(
-            "<a href='h'><div><i>a</i><i>b</i></div>x</a>", "[*a*<em>b</em>x](h)", id="emphasis-adjacent-in-link-html"
+            "<a href='h'><div><i>a</i><i>b</i></div>x</a>", "[*a*<em>b</em> x](h)", id="emphasis-adjacent-in-link-html"
         ),
         pytest.param("<p><i>;</i>i</p>", "<em>;</em>i", id="emphasis-close-punct-before-letter"),
         pytest.param("<p>i<i>;</i></p>", "i<em>;</em>", id="emphasis-open-letter-before-punct"),
diff --git a/tests/test_fuzz_markdown_structure_generation.py b/tests/test_fuzz_markdown_structure_generation.py
index 683d05c17..da4643211 100644
--- a/tests/test_fuzz_markdown_structure_generation.py
+++ b/tests/test_fuzz_markdown_structure_generation.py
@@ -184,6 +184,9 @@ def test_markdown_unsupported_element() -> None:
         pytest.param("<pre>a<p></p>b</pre>", id="empty-block-breaks-code-line"),
         pytest.param("<table><b>x</b></table>", id="foster-parented-emphasis"),
         pytest.param("<table><em>a</em><tr><td>b</td></tr></table>", id="foster-parented-before-rows"),
+        pytest.param("<h3><p>x</p></h3>", id="heading-paragraph"),
+        pytest.param("<h2>a<p>b</p>c</h2>", id="heading-text-around-block"),
+        pytest.param("<h2><div>a</div><div>b</div></h2>", id="heading-sibling-blocks"),
     ],
 )
 def test_markdown_supported_html_meaning(markup: str) -> None:
diff --git a/tools/fuzz/markdown_structure_generators.py b/tools/fuzz/markdown_structure_generators.py
index 44b340c96..9ec3ae9ad 100644
--- a/tools/fuzz/markdown_structure_generators.py
+++ b/tools/fuzz/markdown_structure_generators.py
@@ -227,9 +227,30 @@ def _record(tag: str, element: _TreeNode, children: tuple[_Meaning, ...]) -> tup
         # quote and item content is a flow of blocks; a tight item's single paragraph renders bare (CommonMark 5.1-5.3),
         # so items compare with every inline run wrapped
         return ((tag, (), _flow(children)),)
+    if tag in _HEADINGS:
+        # a heading is one line of inline content (CommonMark 4.2), so its blocks and breaks flatten onto it as spaces
+        return ((tag, (), _line(children)),)
     return ((tag, _attributes(tag, element.attrib), children),)
 
 
+def _line(records: tuple[_Meaning, ...]) -> tuple[_Meaning, ...]:
+    flat: Final[list[_Meaning]] = []
+    for record in records:
+        if record[0] in _FLOW_INLINE and record[0] != "br":
+            flat.append(record)
+        elif record[0] == "br" or record == _BOUNDARY:
+            flat.append(("#text", (("value", " "),), ()))
+        else:
+            flat.extend((("#text", (("value", " "),), ()), *_line(record[2]), ("#text", (("value", " "),), ())))
+    merged: Final[list[_Meaning]] = []
+    for record in flat:
+        if record[0] == "#text" and merged and merged[-1][0] == "#text":
+            merged[-1] = ("#text", (("value", merged[-1][1][0][1] + record[1][0][1]),), ())
+        else:
+            merged.append(record)
+    return _spacing(tuple(merged), preserve=False, inline=False)
+
+
 def _emphasis(tag: str, children: tuple[_Meaning, ...]) -> tuple[_Meaning, ...]:
     if all(record[0] == "#text" and not record[1][0][1].strip(" \t\n\f\r") for record in children):
         return children  # a delimiter run cannot wrap whitespace alone (CommonMark 6.2)
@@ -581,6 +602,7 @@ def _html_grammar() -> Grammar:
 _EMPHASIS: Final = frozenset({"strong", "em", "s"})
 _BLOCKS: Final = frozenset({"p", "ul", "ol", "table"})
 _BOUNDARY: Final[_Meaning] = ("#block", (), ())
+_HEADINGS: Final = frozenset({"h1", "h2", "h3", "h4", "h5", "h6"})
 # the WHATWG content models of the containers whose Markdown syntax can hold nothing else (4.4.5-4.4.8, 4.9)
 _CONTENT_MODEL: Final[dict[str, frozenset[str]]] = {
     "ul": frozenset({"li", "script"}),