diff --git a/AUTHORS b/AUTHORS
index dee73514a..438be7598 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -56,6 +56,7 @@ Benjamin Peterson
 Bernard Pratz
 Bob Ippolito
 Brian Dorsey
+Brian Larsen
 Brian Maissy
 Brian Okken
 Brianna Laugher
diff --git a/changelog/10940.improvement.rst b/changelog/10940.improvement.rst
new file mode 100644
index 000000000..f3e33cbc6
--- /dev/null
+++ b/changelog/10940.improvement.rst
@@ -0,0 +1,3 @@
+Improved verbose output (``-vv``) of ``skip`` and ``xfail`` reasons by performing text wrapping while leaving a clear margin for progress output.
+
+Added :func:`TerminalReporter.wrap_write() <pytest.TerminalReporter.wrap_write>` as a helper for that.
diff --git a/src/_pytest/terminal.py b/src/_pytest/terminal.py
index dfc0fa98e..b7793d398 100644
--- a/src/_pytest/terminal.py
+++ b/src/_pytest/terminal.py
@@ -8,6 +8,7 @@ import datetime
 import inspect
 import platform
 import sys
+import textwrap
 import warnings
 from collections import Counter
 from functools import partial
@@ -426,6 +427,28 @@ class TerminalReporter:
             self._tw.line()
             self.currentfspath = None
 
+    def wrap_write(
+        self,
+        content: str,
+        *,
+        flush: bool = False,
+        margin: int = 8,
+        line_sep: str = "\n",
+        **markup: bool,
+    ) -> None:
+        """Wrap message with margin for progress info."""
+        width_of_current_line = self._tw.width_of_current_line
+        wrapped = line_sep.join(
+            textwrap.wrap(
+                " " * width_of_current_line + content,
+                width=self._screen_width - margin,
+                drop_whitespace=True,
+                replace_whitespace=False,
+            ),
+        )
+        wrapped = wrapped[width_of_current_line:]
+        self._tw.write(wrapped, flush=flush, **markup)
+
     def write(self, content: str, *, flush: bool = False, **markup: bool) -> None:
         self._tw.write(content, flush=flush, **markup)
 
@@ -572,7 +595,7 @@ class TerminalReporter:
                         formatted_reason = f" ({reason})"
 
                     if reason and formatted_reason is not None:
-                        self._tw.write(formatted_reason)
+                        self.wrap_write(formatted_reason)
                 if self._show_progress_info:
                     self._write_progress_information_filling_space()
             else:
diff --git a/testing/test_terminal.py b/testing/test_terminal.py
index 97ce2cb56..c0acb6006 100644
--- a/testing/test_terminal.py
+++ b/testing/test_terminal.py
@@ -387,13 +387,13 @@ class TestTerminal:
                 pytest.xfail("It's 🕙 o'clock")
 
             @pytest.mark.skip(
-                reason="cannot do foobar because baz is missing due to I don't know what"
+                reason="1 cannot do foobar because baz is missing due to I don't know what"
             )
             def test_long_skip():
                 pass
 
             @pytest.mark.xfail(
-                reason="cannot do foobar because baz is missing due to I don't know what"
+                reason="2 cannot do foobar because baz is missing due to I don't know what"
             )
             def test_long_xfail():
                 print(1 / 0)
@@ -417,8 +417,8 @@ class TestTerminal:
         result.stdout.fnmatch_lines(
             common_output
             + [
-                "test_verbose_skip_reason.py::test_long_skip SKIPPED (cannot *...) *",
-                "test_verbose_skip_reason.py::test_long_xfail XFAIL (cannot *...) *",
+                "test_verbose_skip_reason.py::test_long_skip SKIPPED (1 cannot *...) *",
+                "test_verbose_skip_reason.py::test_long_xfail XFAIL (2 cannot *...) *",
             ]
         )
 
@@ -428,12 +428,14 @@ class TestTerminal:
             + [
                 (
                     "test_verbose_skip_reason.py::test_long_skip SKIPPED"
-                    " (cannot do foobar because baz is missing due to I don't know what) *"
+                    " (1 cannot do foobar"
                 ),
+                "because baz is missing due to I don't know what) *",
                 (
                     "test_verbose_skip_reason.py::test_long_xfail XFAIL"
-                    " (cannot do foobar because baz is missing due to I don't know what) *"
+                    " (2 cannot do foobar"
                 ),
+                "because baz is missing due to I don't know what) *",
             ]
         )