diff --git a/.github/scripts/check_issue_readiness.py b/.github/scripts/check_issue_readiness.py
index 208fdb1aa8..f9a4b2c75f 100644
--- a/.github/scripts/check_issue_readiness.py
+++ b/.github/scripts/check_issue_readiness.py
@@ -37,10 +37,12 @@
 BUG_LABEL = "bug"
 ENHANCEMENT_LABEL = "enhancement"
 
-# Issue-form fields render as `### Label` h3 headings. Match case-insensitively
-# and tolerate trailing whitespace/colons. `^###\s+` is specific enough because
-# h1/h2 are not produced by issue forms.
-HEADING_RE = re.compile(r"(?m)^###\s+(.+?)\s*$")
+# Issue-form fields render as `### Label` h3 headings, but free-form issues
+# (and issues edited by agents) commonly use `##` h2 headings. Match any
+# heading level of two or more hashes case-insensitively and tolerate trailing
+# whitespace/colons, so `##` and `###` sections are treated equivalently. A
+# bare `#` (single-hash title) is deliberately not matched.
+HEADING_RE = re.compile(r"(?m)^#{2,}\s+(.+?)\s*$")
 
 # `_No response_` is what GitHub writes for an empty optional form field.
 NO_RESPONSE = "_No response_"
diff --git a/tests/cross/test_check_issue_readiness.py b/tests/cross/test_check_issue_readiness.py
index 67e21112d6..c3b3a54228 100644
--- a/tests/cross/test_check_issue_readiness.py
+++ b/tests/cross/test_check_issue_readiness.py
@@ -53,6 +53,26 @@ def test_extract_sections_splits_on_headings():
     assert sections["beta"] == "\nmore\n"
 
 
+def test_extract_sections_splits_on_h2_headings():
+    sections = extract_sections("## Alpha\n\ntext\n\n## Beta\n\nmore\n")
+    assert sections["alpha"] == "\ntext\n\n"
+    assert sections["beta"] == "\nmore\n"
+
+
+def test_enhancement_h2_headings_passes():
+    body = ENHANCEMENT_READY.replace("### ", "## ")
+    result = evaluate_readiness(body, ["enhancement"])
+    assert result.ready is True
+    assert result.reasons == []
+
+
+def test_bug_h2_headings_passes():
+    body = BUG_READY.replace("### ", "## ")
+    result = evaluate_readiness(body, ["bug"])
+    assert result.ready is True
+    assert result.reasons == []
+
+
 def test_enhancement_ready_passes():
     result = evaluate_readiness(ENHANCEMENT_READY, ["enhancement"])
     assert result.ready is True