diff --git a/changelog/8096.improvement.rst b/changelog/8096.improvement.rst
new file mode 100644
index 00000000000..9b66794b093
--- /dev/null
+++ b/changelog/8096.improvement.rst
@@ -0,0 +1 @@
+Clearer error message for invalid ``-W`` filters, listing valid actions and the ``-Wait`` pitfall.
diff --git a/src/_pytest/config/__init__.py b/src/_pytest/config/__init__.py
index c7bd3e1afab..e4a699c6562 100644
--- a/src/_pytest/config/__init__.py
+++ b/src/_pytest/config/__init__.py
@@ -2320,6 +2320,11 @@ def _strtobool(val: str) -> bool:
         raise ValueError(f"invalid truth value {val!r}")
 
 
+WARNING_FILTER_DOC_URL = (
+    "https://docs.python.org/3/library/warnings.html#describing-warning-filters"
+)
+
+
 @lru_cache(maxsize=50)
 def parse_warning_filter(
     arg: str, *, escape: bool
@@ -2331,6 +2336,8 @@ def parse_warning_filter(
     * Does not apply the filter.
     * Escaping is optional.
     * Raises UsageError so we get nice error messages on failure.
+    * Invalid actions name the valid choices, and hint at the `-W`/`-Wait`
+      short-option pitfall when relevant.
     """
     __tracebackhide__ = True
     error_template = dedent(
@@ -2347,16 +2354,13 @@ def parse_warning_filter(
 
     parts = arg.split(":")
     if len(parts) > 5:
-        doc_url = (
-            "https://docs.python.org/3/library/warnings.html#describing-warning-filters"
-        )
         error = dedent(
             f"""\
             Too many fields ({len(parts)}), expected at most 5 separated by colons:
 
               action:message:category:module:line
 
-            For more information please consult: {doc_url}
+            For more information please consult: {WARNING_FILTER_DOC_URL}
             """
         )
         raise UsageError(error_template.format(error=error))
@@ -2367,7 +2371,16 @@ def parse_warning_filter(
     try:
         action: warnings._ActionKind = warnings._getaction(action_)  # type: ignore[attr-defined]
     except warnings._OptionError as e:
-        raise UsageError(error_template.format(error=str(e))) from None
+        hint = (
+            " (choose from: default, error, ignore, always, all, module, once)."
+            f" See {WARNING_FILTER_DOC_URL}"
+        )
+        if action_.lower() == "ait":
+            hint = (
+                " Note that '-W' takes a value, so '-Wait' is parsed as '-W ait'."
+                + hint
+            )
+        raise UsageError(error_template.format(error=f"{e}{hint}")) from None
     try:
         category: type[Warning] = _resolve_warning_category(category_)
     except ImportError:
diff --git a/testing/test_config.py b/testing/test_config.py
index dad1653e299..23c97b2e0e2 100644
--- a/testing/test_config.py
+++ b/testing/test_config.py
@@ -3112,6 +3112,21 @@ def test_parse_warning_filter_failure(arg: str) -> None:
         parse_warning_filter(arg, escape=True)
 
 
+@pytest.mark.parametrize(
+    "arg, expect_wait_hint",
+    [("ait", True), ("AIT", True), ("FOO", False)],
+)
+def test_parse_warning_filter_invalid_action_hint(
+    arg: str, expect_wait_hint: bool
+) -> None:
+    """Invalid -W actions show valid choices; the -Wait pitfall hint is scoped to that case."""
+    with pytest.raises(
+        pytest.UsageError, match=r"invalid action.*choose from"
+    ) as exc_info:
+        parse_warning_filter(arg, escape=True)
+    assert ("-Wait" in str(exc_info.value)) == expect_wait_hint
+
+
 class TestDebugOptions:
     def test_without_debug_does_not_write_log(self, pytester: Pytester) -> None:
         result = pytester.runpytest()
diff --git a/testing/test_warnings.py b/testing/test_warnings.py
index 0344cb453d8..3728bb844d5 100644
--- a/testing/test_warnings.py
+++ b/testing/test_warnings.py
@@ -563,6 +563,23 @@ def test_invalid_regex_in_filterwarning(self, pytester: Pytester) -> None:
         )
 
 
+def test_dash_w_shows_wait_hint_on_usage_error(pytester: Pytester) -> None:
+    """`-Wait` is parsed as `-W ait`; the hint should point at this."""
+    result = pytester.runpytest("-Wait")
+    assert result.ret == pytest.ExitCode.USAGE_ERROR
+    result.stderr.fnmatch_lines(
+        [
+            "ERROR: while parsing the following warning configuration:",
+            "",
+            "  ait",
+            "",
+            "This error occurred:",
+            "",
+            "invalid action: 'ait'*-Wait*choose from*",
+        ]
+    )
+
+
 @pytest.mark.skip("not relevant until pytest 10.0")
 @pytest.mark.parametrize("change_default", [None, "ini", "cmdline"])
 def test_removed_in_x_warning_as_error(pytester: Pytester, change_default) -> None: