diff --git a/lib/markdown2.py b/lib/markdown2.py
index 66d49a69..a55f7098 100755
--- a/lib/markdown2.py
+++ b/lib/markdown2.py
@@ -630,17 +630,16 @@ def preprocess(self, text: str) -> str:
             (?:
                 {1}:(?:\n+[ \t]+.*)+  # indented lists
             )|(?:
-                (?:{1}:\s+>(?:\n\s+.*)+?)  # multiline long descriptions
-                (?=\n{1}:\s*.*\n|\s*\Z)  # match up until the start of the next key:value definition or the end of the input text
+                {1}:\s+>(?:\n+[ \t]+.*)+  # multiline long descriptions
             )|(?:
-                {1}:(?! >).*\n?  # simple key:value pair, leading spaces allowed
+                {1}:[^\n]*\n?  # simple key:value pair, leading spaces allowed
             )
         ){0}  # optional closing fence
-        '''.format(r'(?:---[\ \t]*\n)?', r'[\S \t]*\w[\S \t]*\s*'), re.MULTILINE | re.VERBOSE
+        '''.format(r'(?:---[\ \t]*\n)?', r'[ \t]*[^\s:\r\n][^:\r\n]*'), re.MULTILINE | re.VERBOSE
     )
 
     _key_val_list_pat = re.compile(
-        r"^-(?:[ \t]*([^\n]*)(?:[ \t]*[:-][ \t]*(\S+))?)(?:\n((?:[ \t]+[^\n]+\n?)+))?",
+        r"^-[ \t]*([^\n]*)(?:\n((?:[ \t]+[^\n]+\n?)+))?",
         re.MULTILINE,
     )
     _key_val_dict_pat = re.compile(
@@ -681,21 +680,28 @@ def parse_structured_value(value: str) -> Union[list[Any], dict[str, Any]]:
             # List
             if vs.startswith("-"):
                 r: list[Any] = []
-                # the regex used has multiple capturing groups, so
-                # returned type from findall will be List[List[str]]
-                match: list[str]
+                # returned type from findall will be list[tuple[str, ...]]
                 for match in re.findall(self._key_val_list_pat, vs):
-                    if match[0] and not match[1] and not match[2]:
-                        r.append(match[0].strip())
-                    elif match[0] == ">" and not match[1] and match[2]:
-                        r.append(match[2].strip())
-                    elif match[0] and match[1]:
-                        r.append({match[0].strip(): match[1].strip()})
-                    elif not match[0] and not match[1] and match[2]:
-                        r.append(parse_structured_value(match[2]))
+                    if len(match) == 2:
+                        val, block = match[0], match[1]
+                        if val and not block:
+                            r.append(val.strip())
+                        elif val == ">" and block:
+                            r.append(block.strip())
+                        elif not val and block:
+                            r.append(parse_structured_value(block))
                     else:
-                        # Broken case
-                        pass
+                        if match[0] and not match[1] and not match[2]:
+                            r.append(match[0].strip())
+                        elif match[0] == ">" and not match[1] and match[2]:
+                            r.append(match[2].strip())
+                        elif match[0] and match[1]:
+                            r.append({match[0].strip(): match[1].strip()})
+                        elif not match[0] and not match[1] and match[2]:
+                            r.append(parse_structured_value(match[2]))
+                        else:
+                            # Broken case
+                            pass
 
                 return r
 
diff --git a/test/test_redos.py b/test/test_redos.py
index 2951ac2d..1866a391 100644
--- a/test/test_redos.py
+++ b/test/test_redos.py
@@ -58,6 +58,14 @@ def issue_707_spaced_attrs():
     return 'x <p' + '  a=1' * 40
 
 
+def issue_metadata_redos():
+    return "---\nkey: -" + " " * 32000 + "\n---\n\n# hello\n"
+
+
+def issue_metadata_list_redos():
+    return "---\nitems:\n  - " + " " * 32000 + "\n---\n\n# hello\n"
+
+
 # whack everything in a dict for easy lookup later on
 CASES = {
     fn.__name__: (fn, extras)
@@ -72,6 +80,8 @@ def issue_707_spaced_attrs():
         (issue_707_unclosed_tags, None),
         (issue_707_namespaced_attrs, None),
         (issue_707_spaced_attrs, None),
+        (issue_metadata_redos, ['metadata']),
+        (issue_metadata_list_redos, ['metadata']),
     ]
 }