diff --git a/CHANGES.md b/CHANGES.md
index 35522381fab..76993ca3fe4 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -22,6 +22,7 @@
 
 <!-- Changes that affect Black's preview style -->
 
+- Fix `fix_fmt_skip_in_one_liners` crashing on `with` statements (#4853)
 - Fix `fix_fmt_skip_in_one_liners` crashing on annotated parameters (#4854)
 
 ### Configuration
diff --git a/src/black/comments.py b/src/black/comments.py
index 13c9926d03b..de1831e4d7c 100644
--- a/src/black/comments.py
+++ b/src/black/comments.py
@@ -650,10 +650,21 @@ 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
+            if (
+                current_node.parent
+                and current_node.parent.type == syms.asexpr_test
+                and current_node.parent.parent
+                and current_node.parent.parent.type == syms.with_stmt
+            ):
+                current_node = 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
+
         # 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/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