diff --git a/AUTHORS b/AUTHORS
index 55b0237ea..7da1f8a0c 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -129,6 +129,7 @@ Feng Ma
 Florian Bruhin
 Florian Dahlitz
 Floris Bruynooghe
+Gabriel Landau
 Gabriel Reis
 Garvit Shubham
 Gene Wood
diff --git a/changelog/10382.bugfix.rst b/changelog/10382.bugfix.rst
new file mode 100644
index 000000000..5876a9a43
--- /dev/null
+++ b/changelog/10382.bugfix.rst
@@ -0,0 +1 @@
+Do not break into pdb when ``raise unittest.SkipTest()`` appears top-level in a file.
diff --git a/src/_pytest/debugging.py b/src/_pytest/debugging.py
index b99c3fe2d..a3f80802c 100644
--- a/src/_pytest/debugging.py
+++ b/src/_pytest/debugging.py
@@ -3,6 +3,7 @@ import argparse
 import functools
 import sys
 import types
+import unittest
 from typing import Any
 from typing import Callable
 from typing import Generator
@@ -293,7 +294,9 @@ class PdbInvoke:
             sys.stdout.write(out)
             sys.stdout.write(err)
         assert call.excinfo is not None
-        _enter_pdb(node, call.excinfo, report)
+
+        if not isinstance(call.excinfo.value, unittest.SkipTest):
+            _enter_pdb(node, call.excinfo, report)
 
     def pytest_internalerror(self, excinfo: ExceptionInfo[BaseException]) -> None:
         tb = _postmortem_traceback(excinfo)
diff --git a/testing/test_debugging.py b/testing/test_debugging.py
index 08ae09658..eecc1e39f 100644
--- a/testing/test_debugging.py
+++ b/testing/test_debugging.py
@@ -20,9 +20,18 @@ def pdb_env(request):
         pytester._monkeypatch.setenv("PDBPP_HIJACK_PDB", "0")
 
 
-def runpdb_and_get_report(pytester: Pytester, source: str):
+def runpdb(pytester: Pytester, source: str):
     p = pytester.makepyfile(source)
-    result = pytester.runpytest_inprocess("--pdb", p)
+    return pytester.runpytest_inprocess("--pdb", p)
+
+
+def runpdb_and_get_stdout(pytester: Pytester, source: str):
+    result = runpdb(pytester, source)
+    return result.stdout.str()
+
+
+def runpdb_and_get_report(pytester: Pytester, source: str):
+    result = runpdb(pytester, source)
     reports = result.reprec.getreports("pytest_runtest_logreport")  # type: ignore[attr-defined]
     assert len(reports) == 3, reports  # setup/call/teardown
     return reports[1]
@@ -124,6 +133,16 @@ class TestPDB:
         assert rep.skipped
         assert len(pdblist) == 0
 
+    def test_pdb_on_top_level_raise_skiptest(self, pytester, pdblist) -> None:
+        stdout = runpdb_and_get_stdout(
+            pytester,
+            """
+            import unittest
+            raise unittest.SkipTest("This is a common way to skip an entire file.")
+        """,
+        )
+        assert "entering PDB" not in stdout, stdout
+
     def test_pdb_on_BdbQuit(self, pytester, pdblist) -> None:
         rep = runpdb_and_get_report(
             pytester,