diff --git a/src/_pytest/skipping.py b/src/_pytest/skipping.py
index 639bf143e53..465e100b2af 100644
--- a/src/_pytest/skipping.py
+++ b/src/_pytest/skipping.py
@@ -204,12 +204,13 @@ def evaluate_skip_marks(item: Item) -> Skip | None:
                 return Skip(reason)
 
     for mark in item.iter_markers(name="skip"):
-        reason = mark.args[0] if mark.args else mark.kwargs.get("reason")
         # Marks applied to a module or class are seen by each of their items,
         # so only warn once per reason.
         warned_reasons = item.config.stash.setdefault(warned_skip_reasons_key, set())
         if (
-            isinstance(reason, str)
+            "reason" not in mark.kwargs
+            and mark.args
+            and isinstance(reason := mark.args[0], str)
             and _looks_like_condition(reason)
             and reason not in warned_reasons
         ):
@@ -217,7 +218,9 @@ def evaluate_skip_marks(item: Item) -> Skip | None:
             item.warn(
                 PytestWarning(
                     f"The reason {reason!r} of pytest.mark.skip looks like a condition. "
-                    "Did you mean pytest.mark.skipif?"
+                    "Did you mean pytest.mark.skipif ?\n"
+                    "If intentional, pass reason as a keyword argument to disable "
+                    "this warning."
                 )
             )
         try:
diff --git a/testing/test_skipping.py b/testing/test_skipping.py
index 0118aed7c88..a8e29fbbd9d 100644
--- a/testing/test_skipping.py
+++ b/testing/test_skipping.py
@@ -1569,16 +1569,17 @@ def test_exit_reason_only():
     result.stdout.fnmatch_lines("*_pytest.outcomes.Exit: foo*")
 
 
-@pytest.mark.parametrize(
-    "reason",
-    [
-        "sys.version_info < (3, 6)",
-        "sys.platform.startswith('win')",
-        "os.name == 'nt'",
-    ],
-)
+SUSPECT_REASONS = [
+    "sys.version_info < (3, 6)",
+    "sys.platform.startswith('win')",
+    "os.name == 'nt'",
+]
+
+
+@pytest.mark.parametrize("reason", SUSPECT_REASONS)
 def test_skip_reason_looks_like_condition_warns(
-    pytester: Pytester, reason: str
+    pytester: Pytester,
+    reason: str,
 ) -> None:
     pytester.makepyfile(
         f"""
@@ -1591,11 +1592,32 @@ def test_func():
     )
     result = pytester.runpytest("-W", "default::pytest.PytestWarning")
     result.stdout.fnmatch_lines(
-        ["*looks like a condition*Did you mean pytest.mark.skipif?"]
+        [
+            "*looks like a condition*Did you mean pytest.mark.skipif ?",
+            "*If intentional, pass reason as a keyword argument to disable this warning.",
+        ]
     )
     result.assert_outcomes(skipped=1, warnings=1)
 
 
+@pytest.mark.parametrize("reason", SUSPECT_REASONS)
+def test_skip_reason_looks_like_condition_kwarg(
+    pytester: Pytester,
+    reason: str,
+) -> None:
+    pytester.makepyfile(
+        f"""
+        import pytest
+
+        @pytest.mark.skip({reason=!r})
+        def test_func():
+            pass
+        """
+    )
+    result = pytester.runpytest("-W", "default::pytest.PytestWarning")
+    result.assert_outcomes(skipped=1, warnings=0)
+
+
 @pytest.mark.parametrize(
     "reason",
     [