diff --git a/Doc/library/pprint.rst b/Doc/library/pprint.rst
index 4f043fbb3a46df..99c7a66dfaf982 100644
--- a/Doc/library/pprint.rst
+++ b/Doc/library/pprint.rst
@@ -46,6 +46,8 @@ Functions
       A file-like object to which the output will be written
       by calling its :meth:`!write` method.
       If ``None`` (the default), :data:`sys.stdout` is used.
+      Characters which cannot be encoded in the encoding of the stream are
+      escaped with backslashes, unless the stream itself handles them.
    :type stream: :term:`file-like object` | None
 
    :param int indent:
@@ -101,6 +103,10 @@ Functions
 
    .. versionadded:: 3.8
 
+   .. versionchanged:: next
+      Unencodable characters are escaped instead of raising
+      :exc:`UnicodeEncodeError`.
+
 
 .. function:: pprint(object, stream=None, indent=1, width=80, depth=None, *, \
                      compact=False, expand=False, sort_dicts=True, \
@@ -238,6 +244,9 @@ PrettyPrinter Objects
    Print the formatted representation of *object* on the configured stream,
    followed by a newline.
 
+   Characters which cannot be encoded in the encoding of the stream are
+   escaped with backslashes, unless the stream itself handles them.
+
 The following methods provide the implementations for the corresponding
 functions of the same names.  Using these methods on an instance is slightly
 more efficient since new :class:`PrettyPrinter` objects don't need to be
diff --git a/Lib/pprint.py b/Lib/pprint.py
index 7355021998081d..5b74b221c43578 100644
--- a/Lib/pprint.py
+++ b/Lib/pprint.py
@@ -111,6 +111,37 @@ def _safe_tuple(t):
     return _safe_key(t[0]), _safe_key(t[1])
 
 
+class _EscapingWriter:
+    """Wrapper which escapes characters unencodable in the stream encoding."""
+
+    def __init__(self, stream, encoding):
+        self._stream = stream
+        self._encoding = encoding
+
+    def write(self, text):
+        text = text.encode(self._encoding, 'backslashreplace')
+        return self._stream.write(text.decode(self._encoding))
+
+    def __getattr__(self, name):
+        return getattr(self._stream, name)
+
+
+def _escape_unencodable(stream):
+    """Return a stream which never fails on unencodable characters.
+
+    The output is intended to be read by humans, so it is better to escape
+    unencodable characters than to fail.  Streams which do not encode the
+    written text, or which already handle unencodable characters, are
+    returned unchanged.
+    """
+    encoding = getattr(stream, 'encoding', None)
+    if encoding is None:
+        return stream
+    if getattr(stream, 'errors', 'strict') != 'strict':
+        return stream
+    return _EscapingWriter(stream, encoding)
+
+
 class PrettyPrinter:
     def __init__(self, indent=1, width=80, depth=None, stream=None, *,
                  compact=False, expand=False, sort_dicts=True,
@@ -171,8 +202,9 @@ def __init__(self, indent=1, width=80, depth=None, stream=None, *,
 
     def pprint(self, object):
         if self._stream is not None:
-            self._format(object, self._stream, 0, 0, {}, 0)
-            self._stream.write("\n")
+            stream = _escape_unencodable(self._stream)
+            self._format(object, stream, 0, 0, {}, 0)
+            stream.write("\n")
 
     def pformat(self, object):
         sio = _StringIO()
diff --git a/Lib/test/test_pprint.py b/Lib/test/test_pprint.py
index 041c2072b9e253..70c18bba6478c5 100644
--- a/Lib/test/test_pprint.py
+++ b/Lib/test/test_pprint.py
@@ -1147,6 +1147,50 @@ def test_str_wrap(self):
             formatted = pprint.pformat([special] * 2, width=width)
             self.assertEqual(eval(formatted), [special] * 2)
 
+    def test_unencodable(self):
+        # with encoding and buffer
+        with io.BytesIO() as bio, \
+             io.TextIOWrapper(bio, encoding='latin1') as stream:
+            stream.write('\xab')
+            pprint.pprint('\xa3\u20ac', stream)
+            stream.flush()
+            self.assertEqual(bio.getvalue(), b"\xab'\xa3\\u20ac'\n")
+            stream.write('\xbb')
+            stream.flush()
+            self.assertEqual(bio.getvalue(), b"\xab'\xa3\\u20ac'\n\xbb")
+        # with encoding but without buffer
+        class MockWriter(list):
+            encoding = 'latin1'
+            errors = 'strict'
+            write = list.append
+        stream = MockWriter()
+        stream.write('\xab')
+        pprint.pprint('\xa3\u20ac', stream)
+        self.assertEqual(''.join(stream), "\xab'\xa3\\u20ac'\n")
+        # without encoding
+        with io.StringIO() as stream:
+            stream.write('\xab')
+            pprint.pprint('\xa3\u20ac', stream)
+            self.assertEqual(stream.getvalue(), "\xab'\xa3\u20ac'\n")
+        # the error handler of the stream is used if it is not strict
+        with io.BytesIO() as bio, \
+             io.TextIOWrapper(bio, encoding='latin1',
+                              errors='replace') as stream:
+            pprint.pprint('\u20ac', stream)
+            stream.flush()
+            self.assertEqual(bio.getvalue(), b"'?'\n")
+
+    def test_unencodable_repr(self):
+        class Surrogate:
+            def __repr__(self):
+                return '\udcff'
+
+        with io.BytesIO() as bio, \
+             io.TextIOWrapper(bio, encoding='utf-8') as stream:
+            pprint.pprint(Surrogate(), stream)
+            stream.flush()
+            self.assertEqual(bio.getvalue(), b"\\udcff\n")
+
     def test_compact(self):
         o = ([list(range(i * i)) for i in range(5)] +
              [list(range(i)) for i in range(6)])
diff --git a/Misc/NEWS.d/next/Library/2026-08-04-22-40-00.gh-issue-63299.pprBsl.rst b/Misc/NEWS.d/next/Library/2026-08-04-22-40-00.gh-issue-63299.pprBsl.rst
new file mode 100644
index 00000000000000..ba82962148256f
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-08-04-22-40-00.gh-issue-63299.pprBsl.rst
@@ -0,0 +1,5 @@
+:func:`pprint.pp`, :func:`pprint.pprint` and
+:meth:`pprint.PrettyPrinter.pprint` no longer fail with
+:exc:`UnicodeEncodeError` if the output contains characters unencodable in the
+encoding of the output stream.  Such characters are now escaped with
+backslashes.