diff --git a/CHANGES.md b/CHANGES.md
index 303d6849bcb..40c8f07e81f 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -30,6 +30,8 @@
 - Standardize type comments to form `# type: <value>` (#4645)
 - Fix `fix_fmt_skip_in_one_liners` preview feature to respect `# fmt: skip` for compound
   statements with semicolon-separated bodies (#4800)
+- Fix `fix_fmt_skip_in_one_liners` crashing on `with` statements and annotated
+  parameters (#4822)
 
 ### Configuration
 
diff --git a/src/black/comments.py b/src/black/comments.py
index 9a89c85e779..52477c3f65f 100644
--- a/src/black/comments.py
+++ b/src/black/comments.py
@@ -587,6 +587,7 @@ def _generate_ignored_nodes_from_fmt_skip(
     comments = list_comments(leaf.prefix, is_endmarker=False, mode=mode)
     if not comments or comment.value != comments[0].value:
         return
+
     if prev_sibling is not None:
         leaf.prefix = leaf.prefix[comment.consumed :]
 
@@ -632,10 +633,22 @@ def _generate_ignored_nodes_from_fmt_skip(
                 current_node.prefix = ""
                 break
 
+            # Special case for with expressions
+            # Without this, we can stuck inside the asexpr_test's children's children
+            parent = current_node.parent
+            if (
+                parent
+                and parent.type == syms.asexpr_test
+                and parent.parent
+                and parent.parent.type == syms.with_stmt
+            ):
+                current_node = parent
+
             ignored_nodes.insert(0, current_node)
 
-            if current_node.prev_sibling is None and current_node.parent is not None:
-                current_node = current_node.parent
+            if current_node.prev_sibling is None and parent is not None:
+                current_node = parent
+
         # Special handling for compound statements with semicolon-separated bodies
         if Preview.fix_fmt_skip_in_one_liners in mode and isinstance(parent, Node):
             body_node = _find_compound_statement_context(parent)
diff --git a/src/black/linegen.py b/src/black/linegen.py
index c2fd5f6858e..b9cd8a27675 100644
--- a/src/black/linegen.py
+++ b/src/black/linegen.py
@@ -440,8 +440,7 @@ def foo(a: int, b: float = 7): ...
 
         def foo(a: (int), b: (float) = 7): ...
         """
-        assert len(node.children) == 3
-        if maybe_make_parens_invisible_in_atom(
+        if len(node.children) == 3 and maybe_make_parens_invisible_in_atom(
             node.children[2], parent=node, mode=self.mode, features=self.features
         ):
             wrap_in_parentheses(node, node.children[2], visible=False)
diff --git a/tests/data/cases/fmtskip10.py b/tests/data/cases/fmtskip10.py
index ed7ffacd07c..98bb843c63f 100644
--- a/tests/data/cases/fmtskip10.py
+++ b/tests/data/cases/fmtskip10.py
@@ -5,6 +5,7 @@ def foo(): return "mock"  # fmt: skip
 if True: print("this"); print("that")  # fmt: skip
 while True: print("loop"); break  # fmt: skip
 for x in [1, 2]: print(x); print("done")  # fmt: skip
+def f(x: int): return x # fmt: skip
 
 j =     1 # fmt: skip
 while j < 10: j += 1  # fmt: skip
diff --git a/tests/data/cases/fmtskip12.py b/tests/data/cases/fmtskip12.py
new file mode 100644
index 00000000000..3af6b4443a1
--- /dev/null
+++ b/tests/data/cases/fmtskip12.py
@@ -0,0 +1,21 @@
+# flags: --preview
+
+with open("file.txt") as f:    content = f.read() # fmt: skip
+
+# Ideally, only the last line would be ignored
+# But ignoring only part of the asexpr_test causes a parse error
+# Same with ignoring the asexpr_test without also ignoring the entire with_stmt
+with open   (
+    "file.txt"   ,
+) as f:    content = f.read() # fmt: skip
+
+# output
+
+with open("file.txt") as f:    content = f.read() # fmt: skip
+
+# Ideally, only the last line would be ignored
+# But ignoring only part of the asexpr_test causes a parse error
+# Same with ignoring the asexpr_test without also ignoring the entire with_stmt
+with open   (
+    "file.txt"   ,
+) as f:    content = f.read() # fmt: skip