diff --git a/IPython/core/doctb.py b/IPython/core/doctb.py
index a4839a7a5f..b56b19769f 100644
--- a/IPython/core/doctb.py
+++ b/IPython/core/doctb.py
@@ -223,7 +223,12 @@ def format_record(self, frame_info: FrameInfo) -> str:
 
         assert frame_info._sd is not None
         result = theme_table[self._theme_name].format(
-            _tokens_filename(True, frame_info.filename, lineno=frame_info.lineno)
+            _tokens_filename(
+                True,
+                frame_info.filename,
+                lineno=frame_info.lineno,
+                compress_user=True,
+            )
         )
         result += ", " if call else ""
         result += f"{call}\n"
diff --git a/IPython/core/tbtools.py b/IPython/core/tbtools.py
index 32f7bc9691..cf4594057b 100644
--- a/IPython/core/tbtools.py
+++ b/IPython/core/tbtools.py
@@ -171,6 +171,7 @@ def _tokens_filename(
     file: str | None,
     *,
     lineno: int | None = None,
+    compress_user: bool = True,
 ) -> TokenStream:
     """
     Format filename lines with custom formatting from caching compiler or `File *.py` by default
@@ -179,6 +180,8 @@ def _tokens_filename(
     ----------
     em: wether bold or not
     file : str
+    compress_user : bool
+        When True (default), apply ``util_path.compress_user`` to the filename.
     """
     Normal = Token.NormalEm if em else Token.Normal
     Filename = Token.FilenameEm if em else Token.Filename
@@ -202,9 +205,9 @@ def _tokens_filename(
                 (Filename, f", line {lineno}"),
             ]
     else:
-        name = util_path.compress_user(
-            py3compat.cast_unicode(file or "", util_path.fs_encoding)
-        )
+        name = py3compat.cast_unicode(file or "", util_path.fs_encoding)
+        if compress_user:
+            name = util_path.compress_user(name)
         if lineno is None:
             return [
                 (Normal, "File "),
diff --git a/IPython/core/ultratb.py b/IPython/core/ultratb.py
index 355ba8858c..c9f0703f1b 100644
--- a/IPython/core/ultratb.py
+++ b/IPython/core/ultratb.py
@@ -260,7 +260,7 @@ def _format_list(self, extracted_list: list[Any]) -> list[str]:
 
             item = theme_table[self._theme_name].format(
                 [(Token.NormalEm if em else Token.Normal, "  ")]
-                + _tokens_filename(em, filename, lineno=lineno)
+                + _tokens_filename(em, filename, lineno=lineno, compress_user=True)
             )
 
             # This seem to be only in xmode plain (%run sinpleer), investigate why not share with verbose.
@@ -332,6 +332,7 @@ def _format_exception_only(
                             True,
                             value.filename,
                             lineno=(None if lineno == "unknown" else lineno),
+                            compress_user=True,
                         )
                         + [(Token, "\n")]
                     )
@@ -615,7 +616,12 @@ def format_record(self, frame_info: FrameInfo) -> str:
             # fast fallback if file is too long
             assert frame_info.filename is not None
             level_tokens = (
-                _tokens_filename(True, frame_info.filename, lineno=frame_info.lineno)
+                _tokens_filename(
+                    True,
+                    frame_info.filename,
+                    lineno=frame_info.lineno,
+                    compress_user=True,
+                )
                 + [
                     (Token, ", " if call else ""),
                     (Token, call),
@@ -658,7 +664,12 @@ def format_record(self, frame_info: FrameInfo) -> str:
             return theme_table[self._theme_name].format(level_tokens + tb_tokens)
         else:
             result = theme_table[self._theme_name].format(
-                _tokens_filename(True, frame_info.filename, lineno=frame_info.lineno)
+                _tokens_filename(
+                    True,
+                    frame_info.filename,
+                    lineno=frame_info.lineno,
+                    compress_user=True,
+                )
             )
             result += ", " if call else ""
             result += f"{call}\n"