diff --git a/Doc/library/traceback.rst b/Doc/library/traceback.rst
index 80dda5ec520d7a..2d5ea19b2cb892 100644
--- a/Doc/library/traceback.rst
+++ b/Doc/library/traceback.rst
@@ -523,27 +523,32 @@ The output for the example would look similar to this:
    *** print_tb:
      File "<doctest...>", line 10, in <module>
        lumberjack()
+       ~~~~~~~~~~^^
    *** print_exception:
    Traceback (most recent call last):
      File "<doctest...>", line 10, in <module>
        lumberjack()
+       ~~~~~~~~~~^^
      File "<doctest...>", line 4, in lumberjack
        bright_side_of_life()
+       ~~~~~~~~~~~~~~~~~~~^^
    IndexError: tuple index out of range
    *** print_exc:
    Traceback (most recent call last):
      File "<doctest...>", line 10, in <module>
        lumberjack()
+       ~~~~~~~~~~^^
      File "<doctest...>", line 4, in lumberjack
        bright_side_of_life()
+       ~~~~~~~~~~~~~~~~~~~^^
    IndexError: tuple index out of range
    *** format_exc, first and last line:
    Traceback (most recent call last):
    IndexError: tuple index out of range
    *** format_exception:
    ['Traceback (most recent call last):\n',
-    '  File "<doctest default[0]>", line 10, in <module>\n    lumberjack()\n',
-    '  File "<doctest default[0]>", line 4, in lumberjack\n    bright_side_of_life()\n',
+    '  File "<doctest default[0]>", line 10, in <module>\n    lumberjack()\n    ~~~~~~~~~~^^\n',
+    '  File "<doctest default[0]>", line 4, in lumberjack\n    bright_side_of_life()\n    ~~~~~~~~~~~~~~~~~~~^^\n',
     '  File "<doctest default[0]>", line 7, in bright_side_of_life\n    return tuple()[0]\n           ~~~~~~~^^^\n',
     'IndexError: tuple index out of range\n']
    *** extract_tb:
@@ -551,8 +556,8 @@ The output for the example would look similar to this:
     <FrameSummary file <doctest...>, line 4 in lumberjack>,
     <FrameSummary file <doctest...>, line 7 in bright_side_of_life>]
    *** format_tb:
-   ['  File "<doctest default[0]>", line 10, in <module>\n    lumberjack()\n',
-    '  File "<doctest default[0]>", line 4, in lumberjack\n    bright_side_of_life()\n',
+   ['  File "<doctest default[0]>", line 10, in <module>\n    lumberjack()\n    ~~~~~~~~~~^^\n',
+    '  File "<doctest default[0]>", line 4, in lumberjack\n    bright_side_of_life()\n    ~~~~~~~~~~~~~~~~~~~^^\n',
     '  File "<doctest default[0]>", line 7, in bright_side_of_life\n    return tuple()[0]\n           ~~~~~~~^^^\n']
    *** tb_lineno: 10
 
diff --git a/Lib/test/test_doctest.py b/Lib/test/test_doctest.py
index 772dbd1d021305..36328f8086c7ad 100644
--- a/Lib/test/test_doctest.py
+++ b/Lib/test/test_doctest.py
@@ -2922,6 +2922,9 @@ def test_unicode(): """
         Traceback (most recent call last):
           File ...
             exec(compile(example.source, filename, "single",
+            ~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+                         compileflags, True), test.globs)
+                         ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
           File "<doctest foo-bär@baz[0]>", line 1, in <module>
             raise Exception('clé')
         Exception: clé
diff --git a/Lib/test/test_exceptions.py b/Lib/test/test_exceptions.py
index 8ccf08703e5389..c57488e44aecc6 100644
--- a/Lib/test/test_exceptions.py
+++ b/Lib/test/test_exceptions.py
@@ -2080,6 +2080,7 @@ def test_multiline_not_highlighted(self):
              """,
                 [
                     '    1 < 2 and',
+                    '    3 > 4',
                     'AssertionError',
                 ],
             ),
@@ -2087,7 +2088,7 @@ def test_multiline_not_highlighted(self):
         for source, expected in cases:
             with self.subTest(source):
                 result = self.write_source(source)
-                self.assertEqual(result[-2:], expected)
+                self.assertEqual(result[-len(expected):], expected)
 
 
 class SyntaxErrorTests(unittest.TestCase):
diff --git a/Lib/test/test_repl.py b/Lib/test/test_repl.py
index 7533376e015e73..a28d1595f44533 100644
--- a/Lib/test/test_repl.py
+++ b/Lib/test/test_repl.py
@@ -161,10 +161,11 @@ def foo(x):
         output = kill_python(p)
         self.assertEqual(p.returncode, 0)
 
-        traceback_lines = output.splitlines()[-7:-1]
+        traceback_lines = output.splitlines()[-8:-1]
         expected_lines = [
             '  File "<stdin>", line 1, in <module>',
             '    foo(0)',
+            '    ~~~^^^',
             '  File "<stdin>", line 2, in foo',
             '    1 / x',
             '    ~~^~~',
diff --git a/Lib/test/test_sys.py b/Lib/test/test_sys.py
index 7f49fb004272bb..0028281596fa4b 100644
--- a/Lib/test/test_sys.py
+++ b/Lib/test/test_sys.py
@@ -1115,8 +1115,10 @@ def check(tracebacklimit, expected):
             b'Traceback (most recent call last):',
             b'  File "<string>", line 8, in <module>',
             b'    f2()',
+            b'    ~~^^',
             b'  File "<string>", line 6, in f2',
             b'    f1()',
+            b'    ~~^^',
             b'  File "<string>", line 4, in f1',
             b'    1 / 0',
             b'    ~~^~~',
@@ -1124,8 +1126,8 @@ def check(tracebacklimit, expected):
         ]
         check(10, traceback)
         check(3, traceback)
-        check(2, traceback[:1] + traceback[3:])
-        check(1, traceback[:1] + traceback[5:])
+        check(2, traceback[:1] + traceback[4:])
+        check(1, traceback[:1] + traceback[7:])
         check(0, [traceback[-1]])
         check(-1, [traceback[-1]])
         check(1<<1000, traceback)
diff --git a/Lib/test/test_traceback.py b/Lib/test/test_traceback.py
index c58d979bdd0115..b60e06ff37f494 100644
--- a/Lib/test/test_traceback.py
+++ b/Lib/test/test_traceback.py
@@ -578,6 +578,7 @@ def f():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f\n'
             '    if True: raise ValueError("basic caret tests")\n'
             '             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
@@ -596,6 +597,7 @@ def f_with_unicode():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f_with_unicode\n'
             '    if True: raise ValueError("Ĥellö Wörld")\n'
             '             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
@@ -613,6 +615,7 @@ def foo(a: THIS_DOES_NOT_EXIST ) -> int:
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f_with_type\n'
             '    def foo(a: THIS_DOES_NOT_EXIST ) -> int:\n'
             '               ^^^^^^^^^^^^^^^^^^^\n'
@@ -633,9 +636,14 @@ def f_with_multiline():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f_with_multiline\n'
             '    if True: raise ValueError(\n'
-            '             ^^^^^^^^^^^^^^^^^'
+            '             ^^^^^^^^^^^^^^^^^\n'
+            '        "error over multiple lines"\n'
+            '        ^^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
+            '    )\n'
+            '    ^'
         )
         result_lines = self.get_exception(f_with_multiline)
         self.assertEqual(result_lines, expected_f.splitlines())
@@ -664,9 +672,10 @@ def f_with_multiline():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_multiline\n'
             '    return compile(code, "?", "exec")\n'
-            '           ^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
+            '           ~~~~~~~^^^^^^^^^^^^^^^^^^^\n'
             '  File "?", line 7\n'
             '    foo(a, z\n'
             '           ^'
@@ -689,9 +698,12 @@ def f_with_multiline():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_multiline\n'
             '    2 + 1 /\n'
-            '        ^^^'
+            '        ~~^\n'
+            '    0\n'
+            '    ~'
         )
         result_lines = self.get_exception(f_with_multiline)
         self.assertEqual(result_lines, expected_f.splitlines())
@@ -706,6 +718,7 @@ def f_with_binary_operator():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_binary_operator\n'
             '    return 10 + divisor / 0 + 30\n'
             '                ~~~~~~~~^~~\n'
@@ -723,6 +736,7 @@ def f_with_binary_operator():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_binary_operator\n'
             '    return 10 + áóí / 0 + 30\n'
             '                ~~~~^~~\n'
@@ -740,6 +754,7 @@ def f_with_binary_operator():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_binary_operator\n'
             '    return 10 + divisor // 0 + 30\n'
             '                ~~~~~~~~^^~~\n'
@@ -751,16 +766,102 @@ def test_caret_for_binary_operators_with_spaces_and_parenthesis(self):
         def f_with_binary_operator():
             a = 1
             b = ""
-            return ( a   )   + b
+            return ( a   )   +b
 
         lineno_f = f_with_binary_operator.__code__.co_firstlineno
         expected_error = (
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+3}, in f_with_binary_operator\n'
-            '    return ( a   )   + b\n'
-            '           ~~~~~~~~~~^~~\n'
+            '    return ( a   )   +b\n'
+            '           ~~~~~~~~~~^~\n'
+        )
+        result_lines = self.get_exception(f_with_binary_operator)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_binary_operators_multiline(self):
+        def f_with_binary_operator():
+            b = 1
+            c = ""
+            a = b    \
+         +\
+               c  # test
+            return a
+
+        lineno_f = f_with_binary_operator.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+3}, in f_with_binary_operator\n'
+            '       a = b    \\\n'
+            '           ~~~~~~\n'
+            '    +\\\n'
+            '    ^~\n'
+            '          c  # test\n'
+            '          ~\n'
+        )
+        result_lines = self.get_exception(f_with_binary_operator)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_binary_operators_multiline_two_char(self):
+        def f_with_binary_operator():
+            b = 1
+            c = ""
+            a = (
+                (b  # test +
+                    )  \
+                # +
+            << (c  # test
+                \
+            )  # test
+            )
+            return a
+
+        lineno_f = f_with_binary_operator.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+4}, in f_with_binary_operator\n'
+            '        (b  # test +\n'
+            '        ~~~~~~~~~~~~\n'
+            '            )  \\\n'
+            '            ~~~~\n'
+            '        # +\n'
+            '        ~~~\n'
+            '    << (c  # test\n'
+            '    ^^~~~~~~~~~~~\n'
+            '        \\\n'
+            '        ~\n'
+            '    )  # test\n'
+            '    ~\n'
+        )
+        result_lines = self.get_exception(f_with_binary_operator)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_binary_operators_multiline_with_unicode(self):
+        def f_with_binary_operator():
+            b = 1
+            a = ("ááá" +
+                "áá") + b
+            return a
+
+        lineno_f = f_with_binary_operator.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+2}, in f_with_binary_operator\n'
+            '    a = ("ááá" +\n'
+            '        ~~~~~~~~\n'
+            '        "áá") + b\n'
+            '        ~~~~~~^~~\n'
         )
         result_lines = self.get_exception(f_with_binary_operator)
         self.assertEqual(result_lines, expected_error.splitlines())
@@ -775,6 +876,7 @@ def f_with_subscript():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_subscript\n'
             "    return some_dict['x']['y']['z']\n"
             '           ~~~~~~~~~~~~~~~~~~~^^^^^\n'
@@ -792,6 +894,7 @@ def f_with_subscript():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_subscript\n'
             "    return some_dict['ó']['á']['í']['beta']\n"
             '           ~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^\n'
@@ -810,6 +913,7 @@ def f_with_binary_operator():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+3}, in f_with_binary_operator\n'
             '    return b     [    a  ] + c\n'
             '           ~~~~~~^^^^^^^^^\n'
@@ -817,6 +921,226 @@ def f_with_binary_operator():
         result_lines = self.get_exception(f_with_binary_operator)
         self.assertEqual(result_lines, expected_error.splitlines())
 
+    def test_caret_for_subscript_multiline(self):
+        def f_with_subscript():
+            bbbbb = {}
+            ccc = 1
+            ddd = 2
+            b = bbbbb \
+                [  ccc # test
+
+                 + ddd  \
+
+                ] # test
+            return b
+
+        lineno_f = f_with_subscript.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+4}, in f_with_subscript\n'
+            '    b = bbbbb \\\n'
+            '        ~~~~~~~\n'
+            '        [  ccc # test\n'
+            '        ^^^^^^^^^^^^^\n'
+            '    \n'
+            '    \n'
+            '         + ddd  \\\n'
+            '         ^^^^^^^^\n'
+            '    \n'
+            '    \n'
+            '        ] # test\n'
+            '        ^\n'
+        )
+        result_lines = self.get_exception(f_with_subscript)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_call(self):
+        def f_with_call():
+            def f1(a):
+                def f2(b):
+                    raise RuntimeError("fail")
+                return f2
+            return f1("x")("y")
+
+        lineno_f = f_with_call.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+5}, in f_with_call\n'
+            '    return f1("x")("y")\n'
+            '           ~~~~~~~^^^^^\n'
+            f'  File "{__file__}", line {lineno_f+3}, in f2\n'
+            '    raise RuntimeError("fail")\n'
+        )
+        result_lines = self.get_exception(f_with_call)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_call_unicode(self):
+        def f_with_call():
+            def f1(a):
+                def f2(b):
+                    raise RuntimeError("fail")
+                return f2
+            return f1("ó")("á")
+
+        lineno_f = f_with_call.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+5}, in f_with_call\n'
+            '    return f1("ó")("á")\n'
+            '           ~~~~~~~^^^^^\n'
+            f'  File "{__file__}", line {lineno_f+3}, in f2\n'
+            '    raise RuntimeError("fail")\n'
+        )
+        result_lines = self.get_exception(f_with_call)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_call_with_spaces_and_parenthesis(self):
+        def f_with_binary_operator():
+            def f(a):
+                raise RuntimeError("fail")
+            return f     (    "x"  ) + 2
+
+        lineno_f = f_with_binary_operator.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+3}, in f_with_binary_operator\n'
+            '    return f     (    "x"  ) + 2\n'
+            '           ~~~~~~^^^^^^^^^^^\n'
+            f'  File "{__file__}", line {lineno_f+2}, in f\n'
+            '    raise RuntimeError("fail")\n'
+        )
+        result_lines = self.get_exception(f_with_binary_operator)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_caret_for_call_multiline(self):
+        def f_with_call():
+            class C:
+                def y(self, a):
+                    def f(b):
+                        raise RuntimeError("fail")
+                    return f
+            def g(x):
+                return C()
+            a = (g(1).y)(
+                2
+            )(3)(4)
+            return a
+
+        lineno_f = f_with_call.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+8}, in f_with_call\n'
+            '    a = (g(1).y)(\n'
+            '        ~~~~~~~~~\n'
+            '        2\n'
+            '        ~\n'
+            '    )(3)(4)\n'
+            '    ~^^^\n'
+            f'  File "{__file__}", line {lineno_f+4}, in f\n'
+            '    raise RuntimeError("fail")\n'
+        )
+        result_lines = self.get_exception(f_with_call)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_many_lines(self):
+        def f():
+            x = 1
+            if True: x += (
+                "a" +
+                "a"
+            )  # test
+
+        lineno_f = f.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+2}, in f\n'
+            '    if True: x += (\n'
+            '             ^^^^^^\n'
+            '    ...<2 lines>...\n'
+            '    )  # test\n'
+            '    ^\n'
+        )
+        result_lines = self.get_exception(f)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_many_lines_no_caret(self):
+        def f():
+            x = 1
+            x += (
+                "a" +
+                "a"
+            )
+
+        lineno_f = f.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+2}, in f\n'
+            '    x += (\n'
+            '    ...<2 lines>...\n'
+            '    )\n'
+        )
+        result_lines = self.get_exception(f)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
+    def test_many_lines_binary_op(self):
+        def f_with_binary_operator():
+            b = 1
+            c = "a"
+            a = (
+                b +
+                b
+            ) + (
+                c +
+                c +
+                c
+            )
+            return a
+
+        lineno_f = f_with_binary_operator.__code__.co_firstlineno
+        expected_error = (
+            'Traceback (most recent call last):\n'
+            f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
+            '    callable()\n'
+            '    ~~~~~~~~^^\n'
+            f'  File "{__file__}", line {lineno_f+3}, in f_with_binary_operator\n'
+            '    a = (\n'
+            '        ~\n'
+            '        b +\n'
+            '        ~~~\n'
+            '        b\n'
+            '        ~\n'
+            '    ) + (\n'
+            '    ~~^~~\n'
+            '        c +\n'
+            '        ~~~\n'
+            '    ...<2 lines>...\n'
+            '    )\n'
+            '    ~\n'
+        )
+        result_lines = self.get_exception(f_with_binary_operator)
+        self.assertEqual(result_lines, expected_error.splitlines())
+
     def test_traceback_specialization_with_syntax_error(self):
         bytecode = compile("1 / 0 / 1 / 2\n", TESTFN, "exec")
 
@@ -833,6 +1157,7 @@ def test_traceback_specialization_with_syntax_error(self):
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{TESTFN}", line {lineno_f}, in <module>\n'
             "    1 $ 0 / 1 / 2\n"
             '    ^^^^^\n'
@@ -855,6 +1180,7 @@ def test_traceback_very_long_line(self):
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{TESTFN}", line {lineno_f}, in <module>\n'
             f'    {source}\n'
             f'    {" "*len("if True: ") + "^"*256}\n'
@@ -872,6 +1198,7 @@ def f_with_subscript():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_f+2}, in f_with_subscript\n'
             "    some_dict['x']['y']['z']\n"
             '    ~~~~~~~~~~~~~~~~~~~^^^^^\n'
@@ -891,6 +1218,7 @@ def exc():
              f'  + Exception Group Traceback (most recent call last):\n'
              f'  |   File "{__file__}", line {self.callable_line}, in get_exception\n'
              f'  |     callable()\n'
+             f'  |     ~~~~~~~~^^\n'
              f'  |   File "{__file__}", line {exc.__code__.co_firstlineno + 1}, in exc\n'
              f'  |     if True: raise ExceptionGroup("eg", [ValueError(1), TypeError(2)])\n'
              f'  |              ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
@@ -956,6 +1284,7 @@ def g(): pass
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_applydescs + 1}, in applydecs\n'
             '    @dec_error\n'
             '     ^^^^^^^^^\n'
@@ -974,6 +1303,7 @@ class A: pass
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
             '    callable()\n'
+            '    ~~~~~~~~^^\n'
             f'  File "{__file__}", line {lineno_applydescs_class + 1}, in applydecs_class\n'
             '    @dec_error\n'
             '     ^^^^^^^^^\n'
@@ -992,6 +1322,7 @@ def f():
             "Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             "    callable()",
+            "    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 2}, in f",
             "    .method",
             "     ^^^^^^",
@@ -1008,6 +1339,7 @@ def f():
             "Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             "    callable()",
+            "    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 2}, in f",
             "    method",
         ]
@@ -1023,6 +1355,7 @@ def f():
             "Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             "    callable()",
+            "    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 2}, in f",
             "    . method",
             "      ^^^^^^",
@@ -1038,6 +1371,7 @@ def f():
             "Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             "    callable()",
+            "    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 1}, in f",
             "    ｗｉｄｔｈ",
         ]
@@ -1054,6 +1388,7 @@ def f():
             "Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             "    callable()",
+            "    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 2}, in f",
             "    raise ValueError(ｗｉｄｔｈ)",
         ]
@@ -1072,9 +1407,12 @@ def f():
             "Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             "    callable()",
+            "    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 4}, in f",
             f"    print(1, ｗｗｗ(",
-            f"             ^^^^^^^",
+            f"             ~~~~~~^",
+            f"            ｔｈ))",
+            f"            ^^^^^",
         ]
         self.assertEqual(actual, expected)
 
@@ -1089,6 +1427,7 @@ def f():
             f"Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             f"    callable()",
+            f"    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 3}, in f",
             f"    return 说明说明 / şçöğıĤellö",
             f"           ~~~~~~~~~^~~~~~~~~~~~",
@@ -1105,6 +1444,7 @@ def f():
             f"Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             f"    callable()",
+            f"    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 1}, in f",
             f'    return "✨🐍" + func_说明说明("📗🚛",',
             f"                    ^^^^^^^^^^^^^",
@@ -1127,6 +1467,7 @@ def f():
             f"Traceback (most recent call last):",
             f"  File \"{__file__}\", line {self.callable_line}, in get_exception",
             f"    callable()",
+            f"    ~~~~~~~~^^",
             f"  File \"{__file__}\", line {f.__code__.co_firstlineno + 8}, in f",
             f'    return my_dct["✨🚛✨"]["说明"]["🐍"]["说明"]["🐍🐍"]',
             f"           ~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^",
@@ -1141,6 +1482,7 @@ def f():
         expected = ['Traceback (most recent call last):',
             f'  File "{__file__}", line {self.callable_line}, in get_exception',
             '    callable()',
+            '    ~~~~~~~~^^',
             f'  File "{__file__}", line {f.__code__.co_firstlineno + 1}, in f',
             '    raise MemoryError()']
         self.assertEqual(actual, expected)
@@ -1187,6 +1529,14 @@ class TracebackFormatMixin:
     def some_exception(self):
         raise KeyError('blah')
 
+    def _filter_debug_ranges(self, expected):
+        return [line for line in expected if not set(line.strip()) <= set("^~")]
+
+    def _maybe_filter_debug_ranges(self, expected):
+        if not self.DEBUG_RANGES:
+            return self._filter_debug_ranges(expected)
+        return expected
+
     @cpython_only
     def check_traceback_format(self, cleanup_func=None):
         from _testcapi import traceback_print
@@ -1199,6 +1549,11 @@ def check_traceback_format(self, cleanup_func=None):
                 cleanup_func(tb.tb_next)
             traceback_fmt = 'Traceback (most recent call last):\n' + \
                             ''.join(traceback.format_tb(tb))
+            # clear caret lines from traceback_fmt since internal API does
+            # not emit them
+            traceback_fmt = "\n".join(
+                self._filter_debug_ranges(traceback_fmt.splitlines())
+            ) + "\n"
             file_ = StringIO()
             traceback_print(tb, file_)
             python_fmt  = file_.getvalue()
@@ -1291,12 +1646,16 @@ def f():
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {lineno_f+5}, in _check_recursive_traceback_display\n'
             '    f()\n'
+            '    ~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f\n'
             '    f()\n'
+            '    ~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f\n'
             '    f()\n'
+            '    ~^^\n'
             f'  File "{__file__}", line {lineno_f+1}, in f\n'
             '    f()\n'
+            '    ~^^\n'
             # XXX: The following line changes depending on whether the tests
             # are run through the interactive interpreter or with -m
             # It also varies depending on the platform (stack size)
@@ -1305,7 +1664,7 @@ def f():
             'RecursionError: maximum recursion depth exceeded\n'
         )
 
-        expected = result_f.splitlines()
+        expected = self._maybe_filter_debug_ranges(result_f.splitlines())
         actual = stderr_f.getvalue().splitlines()
 
         # Check the output text matches expectations
@@ -1337,13 +1696,13 @@ def g(count=10):
         result_g = (
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             '  [Previous line repeated 7 more times]\n'
             f'  File "{__file__}", line {lineno_g+3}, in g\n'
             '    raise ValueError\n'
@@ -1353,11 +1712,10 @@ def g(count=10):
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {lineno_g+7}, in _check_recursive_traceback_display\n'
             '    g()\n'
+            '    ~^^\n'
         )
-        expected = (tb_line + result_g).splitlines()
+        expected = self._maybe_filter_debug_ranges((tb_line + result_g).splitlines())
         actual = stderr_g.getvalue().splitlines()
-        if not self.DEBUG_RANGES:
-            expected = [line for line in expected if not set(line.strip()) == {"^"}]
         self.assertEqual(actual, expected)
 
         # Check 2 different repetitive sections
@@ -1379,23 +1737,23 @@ def h(count=10):
             'Traceback (most recent call last):\n'
             f'  File "{__file__}", line {lineno_h+7}, in _check_recursive_traceback_display\n'
             '    h()\n'
+            '    ~^^\n'
             f'  File "{__file__}", line {lineno_h+2}, in h\n'
             '    return h(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_h+2}, in h\n'
             '    return h(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_h+2}, in h\n'
             '    return h(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             '  [Previous line repeated 7 more times]\n'
             f'  File "{__file__}", line {lineno_h+3}, in h\n'
             '    g()\n'
+            '    ~^^\n'
         )
-        expected = (result_h + result_g).splitlines()
+        expected = self._maybe_filter_debug_ranges((result_h + result_g).splitlines())
         actual = stderr_h.getvalue().splitlines()
-        if not self.DEBUG_RANGES:
-            expected = [line for line in expected if not set(line.strip()) == {"^"}]
         self.assertEqual(actual, expected)
 
         # Check the boundary conditions. First, test just below the cutoff.
@@ -1409,26 +1767,25 @@ def h(count=10):
         result_g = (
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+3}, in g\n'
             '    raise ValueError\n'
             'ValueError\n'
         )
         tb_line = (
             'Traceback (most recent call last):\n'
-            f'  File "{__file__}", line {lineno_g+81}, in _check_recursive_traceback_display\n'
+            f'  File "{__file__}", line {lineno_g+80}, in _check_recursive_traceback_display\n'
             '    g(traceback._RECURSIVE_CUTOFF)\n'
+            '    ~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
         )
-        expected = (tb_line + result_g).splitlines()
+        expected = self._maybe_filter_debug_ranges((tb_line + result_g).splitlines())
         actual = stderr_g.getvalue().splitlines()
-        if not self.DEBUG_RANGES:
-            expected = [line for line in expected if not set(line.strip()) == {"^"}]
         self.assertEqual(actual, expected)
 
         # Second, test just above the cutoff.
@@ -1442,13 +1799,13 @@ def h(count=10):
         result_g = (
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             f'  File "{__file__}", line {lineno_g+2}, in g\n'
             '    return g(count-1)\n'
-            '           ^^^^^^^^^^\n'
+            '           ~^^^^^^^^^\n'
             '  [Previous line repeated 1 more time]\n'
             f'  File "{__file__}", line {lineno_g+3}, in g\n'
             '    raise ValueError\n'
@@ -1456,13 +1813,12 @@ def h(count=10):
         )
         tb_line = (
             'Traceback (most recent call last):\n'
-            f'  File "{__file__}", line {lineno_g+114}, in _check_recursive_traceback_display\n'
+            f'  File "{__file__}", line {lineno_g+112}, in _check_recursive_traceback_display\n'
             '    g(traceback._RECURSIVE_CUTOFF + 1)\n'
+            '    ~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n'
         )
-        expected = (tb_line + result_g).splitlines()
+        expected = self._maybe_filter_debug_ranges((tb_line + result_g).splitlines())
         actual = stderr_g.getvalue().splitlines()
-        if not self.DEBUG_RANGES:
-            expected = [line for line in expected if not set(line.strip()) == {"^"}]
         self.assertEqual(actual, expected)
 
     @requires_debug_ranges()
@@ -1942,6 +2298,7 @@ def exc():
              f'  + Exception Group Traceback (most recent call last):\n'
              f'  |   File "{__file__}", line {self.callable_line}, in get_exception\n'
              f'  |     exception_or_callable()\n'
+             f'  |     ~~~~~~~~~~~~~~~~~~~~~^^\n'
              f'  |   File "{__file__}", line {exc.__code__.co_firstlineno + 1}, in exc\n'
              f'  |     raise ExceptionGroup("eg", [ValueError(1), TypeError(2)])\n'
              f'  | ExceptionGroup: eg (2 sub-exceptions)\n'
@@ -1977,6 +2334,7 @@ def exc():
                     f'  + Exception Group Traceback (most recent call last):\n'
                     f'  |   File "{__file__}", line {self.callable_line}, in get_exception\n'
                     f'  |     exception_or_callable()\n'
+                    f'  |     ~~~~~~~~~~~~~~~~~~~~~^^\n'
                     f'  |   File "{__file__}", line {exc.__code__.co_firstlineno + 5}, in exc\n'
                     f'  |     raise EG("eg2", [ValueError(3), TypeError(4)]) from e\n'
                     f'  | ExceptionGroup: eg2 (2 sub-exceptions)\n'
@@ -2028,6 +2386,7 @@ def exc():
              f'Traceback (most recent call last):\n'
              f'  File "{__file__}", line {self.callable_line}, in get_exception\n'
              f'    exception_or_callable()\n'
+             f'    ~~~~~~~~~~~~~~~~~~~~~^^\n'
              f'  File "{__file__}", line {exc.__code__.co_firstlineno + 8}, in exc\n'
              f'    raise ImportError(5)\n'
              f'ImportError: 5\n')
@@ -2074,6 +2433,7 @@ def exc():
                     f'  + Exception Group Traceback (most recent call last):\n'
                     f'  |   File "{__file__}", line {self.callable_line}, in get_exception\n'
                     f'  |     exception_or_callable()\n'
+                    f'  |     ~~~~~~~~~~~~~~~~~~~~~^^\n'
                     f'  |   File "{__file__}", line {exc.__code__.co_firstlineno + 11}, in exc\n'
                     f'  |     raise EG("top", [VE(5)])\n'
                     f'  | ExceptionGroup: top (1 sub-exception)\n'
@@ -2233,6 +2593,7 @@ def exc():
         expected = (f'  + Exception Group Traceback (most recent call last):\n'
                     f'  |   File "{__file__}", line {self.callable_line}, in get_exception\n'
                     f'  |     exception_or_callable()\n'
+                    f'  |     ~~~~~~~~~~~~~~~~~~~~~^^\n'
                     f'  |   File "{__file__}", line {exc.__code__.co_firstlineno + 9}, in exc\n'
                     f'  |     raise ExceptionGroup("nested", excs)\n'
                     f'  | ExceptionGroup: nested (2 sub-exceptions)\n'
@@ -2284,6 +2645,7 @@ def exc():
         expected = (f'  + Exception Group Traceback (most recent call last):\n'
                     f'  |   File "{__file__}", line {self.callable_line}, in get_exception\n'
                     f'  |     exception_or_callable()\n'
+                    f'  |     ~~~~~~~~~~~~~~~~~~~~~^^\n'
                     f'  |   File "{__file__}", line {exc.__code__.co_firstlineno + 10}, in exc\n'
                     f'  |     raise ExceptionGroup("nested", excs)\n'
                     f'  | ExceptionGroup: nested (2 sub-exceptions)\n'
@@ -2552,7 +2914,7 @@ def test_basics(self):
     def test_lazy_lines(self):
         linecache.clearcache()
         f = traceback.FrameSummary("f", 1, "dummy", lookup_line=False)
-        self.assertEqual(None, f._line)
+        self.assertEqual(None, f._lines)
         linecache.lazycache("f", globals())
         self.assertEqual(
             '"""Test cases for traceback module"""',
@@ -3143,6 +3505,7 @@ def test_exception_group_format(self):
                     f'      | Traceback (most recent call last):',
                     f'      |   File "{__file__}", line {lno_g+9}, in _get_exception_group',
                     f'      |     f()',
+                    f'      |     ~^^',
                     f'      |   File "{__file__}", line {lno_f+1}, in f',
                     f'      |     1/0',
                     f'      |     ~^~',
@@ -3151,6 +3514,7 @@ def test_exception_group_format(self):
                     f'      | Traceback (most recent call last):',
                     f'      |   File "{__file__}", line {lno_g+13}, in _get_exception_group',
                     f'      |     g(42)',
+                    f'      |     ~^^^^',
                     f'      |   File "{__file__}", line {lno_g+1}, in g',
                     f'      |     raise ValueError(v)',
                     f'      | ValueError: 42',
@@ -3159,6 +3523,7 @@ def test_exception_group_format(self):
                     f'    | Traceback (most recent call last):',
                     f'    |   File "{__file__}", line {lno_g+20}, in _get_exception_group',
                     f'    |     g(24)',
+                    f'    |     ~^^^^',
                     f'    |   File "{__file__}", line {lno_g+1}, in g',
                     f'    |     raise ValueError(v)',
                     f'    | ValueError: 24',
diff --git a/Lib/test/test_warnings/__init__.py b/Lib/test/test_warnings/__init__.py
index 232480c46e0a00..50b0f3fff04c57 100644
--- a/Lib/test/test_warnings/__init__.py
+++ b/Lib/test/test_warnings/__init__.py
@@ -1260,8 +1260,8 @@ def test_conflicting_envvar_and_command_line(self):
              b"  File \"<string>\", line 1, in <module>",
              b'    import sys, warnings; sys.stdout.write(str(sys.warnoptions)); warnings.w'
              b"arn('Message', DeprecationWarning)",
-             b'                                                                  ^^^^^^^^^^'
-             b'^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^',
+             b'                                                                  ~~~~~~~~~~'
+             b'~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^',
              b"DeprecationWarning: Message"])
 
     def test_default_filter_configuration(self):
diff --git a/Lib/traceback.py b/Lib/traceback.py
index 5d83f85ac3edb0..a0485a7023d07d 100644
--- a/Lib/traceback.py
+++ b/Lib/traceback.py
@@ -274,7 +274,7 @@ class FrameSummary:
     """
 
     __slots__ = ('filename', 'lineno', 'end_lineno', 'colno', 'end_colno',
-                 'name', '_line', 'locals')
+                 'name', '_lines', '_lines_dedented', 'locals')
 
     def __init__(self, filename, lineno, name, *, lookup_line=True,
             locals=None, line=None,
@@ -290,15 +290,16 @@ def __init__(self, filename, lineno, name, *, lookup_line=True,
         """
         self.filename = filename
         self.lineno = lineno
+        self.end_lineno = lineno if end_lineno is None else end_lineno
+        self.colno = colno
+        self.end_colno = end_colno
         self.name = name
-        self._line = line
+        self._lines = line
+        self._lines_dedented = None
         if lookup_line:
             self.line
         self.locals = {k: _safe_string(v, 'local', func=repr)
             for k, v in locals.items()} if locals else None
-        self.end_lineno = end_lineno
-        self.colno = colno
-        self.end_colno = end_colno
 
     def __eq__(self, other):
         if isinstance(other, FrameSummary):
@@ -323,19 +324,39 @@ def __repr__(self):
     def __len__(self):
         return 4
 
+    def _set_lines(self):
+        if (
+            self._lines is None
+            and self.lineno is not None
+            and self.end_lineno is not None
+        ):
+            lines = []
+            for lineno in range(self.lineno, self.end_lineno + 1):
+                # treat errors (empty string) and empty lines (newline) as the same
+                lines.append(linecache.getline(self.filename, lineno).rstrip())
+            self._lines = "\n".join(lines) + "\n"
+
     @property
-    def _original_line(self):
+    def _original_lines(self):
         # Returns the line as-is from the source, without modifying whitespace.
-        self.line
-        return self._line
+        self._set_lines()
+        return self._lines
+
+    @property
+    def _dedented_lines(self):
+        # Returns _original_lines, but dedented
+        self._set_lines()
+        if self._lines_dedented is None and self._lines is not None:
+            self._lines_dedented = textwrap.dedent(self._lines)
+        return self._lines_dedented
 
     @property
     def line(self):
-        if self._line is None:
-            if self.lineno is None:
-                return None
-            self._line = linecache.getline(self.filename, self.lineno)
-        return self._line.strip()
+        self._set_lines()
+        if self._lines is None:
+            return None
+        # return only the first line, stripped
+        return self._lines.partition("\n")[0].strip()
 
 
 def walk_stack(f):
@@ -487,56 +508,135 @@ def format_frame_summary(self, frame_summary):
             filename = "<stdin>"
         row.append('  File "{}", line {}, in {}\n'.format(
             filename, frame_summary.lineno, frame_summary.name))
-        if frame_summary.line:
-            stripped_line = frame_summary.line.strip()
-            row.append('    {}\n'.format(stripped_line))
-
-            line = frame_summary._original_line
-            orig_line_len = len(line)
-            frame_line_len = len(frame_summary.line.lstrip())
-            stripped_characters = orig_line_len - frame_line_len
+        if frame_summary._dedented_lines and frame_summary._dedented_lines.strip():
             if (
-                frame_summary.colno is not None
-                and frame_summary.end_colno is not None
+                frame_summary.colno is None or
+                frame_summary.end_colno is None
             ):
-                start_offset = _byte_offset_to_character_offset(
-                    line, frame_summary.colno)
-                end_offset = _byte_offset_to_character_offset(
-                    line, frame_summary.end_colno)
-                code_segment = line[start_offset:end_offset]
+                # only output first line if column information is missing
+                row.append(textwrap.indent(frame_summary.line, '    ') + "\n")
+            else:
+                # get first and last line
+                all_lines_original = frame_summary._original_lines.splitlines()
+                first_line = all_lines_original[0]
+                # assume all_lines_original has enough lines (since we constructed it)
+                last_line = all_lines_original[frame_summary.end_lineno - frame_summary.lineno]
+
+                # character index of the start/end of the instruction
+                start_offset = _byte_offset_to_character_offset(first_line, frame_summary.colno)
+                end_offset = _byte_offset_to_character_offset(last_line, frame_summary.end_colno)
+
+                all_lines = frame_summary._dedented_lines.splitlines()[
+                    :frame_summary.end_lineno - frame_summary.lineno + 1
+                ]
 
+                # adjust start/end offset based on dedent
+                dedent_characters = len(first_line) - len(all_lines[0])
+                start_offset = max(0, start_offset - dedent_characters)
+                end_offset = max(0, end_offset - dedent_characters)
+
+                # When showing this on a terminal, some of the non-ASCII characters
+                # might be rendered as double-width characters, so we need to take
+                # that into account when calculating the length of the line.
+                dp_start_offset = _display_width(all_lines[0], offset=start_offset)
+                dp_end_offset = _display_width(all_lines[-1], offset=end_offset)
+
+                # get exact code segment corresponding to the instruction
+                segment = "\n".join(all_lines)
+                segment = segment[start_offset:len(segment) - (len(all_lines[-1]) - end_offset)]
+
+                # attempt to parse for anchors
                 anchors = None
-                if frame_summary.lineno == frame_summary.end_lineno:
-                    with suppress(Exception):
-                        anchors = _extract_caret_anchors_from_line_segment(code_segment)
-                else:
-                    # Don't count the newline since the anchors only need to
-                    # go up until the last character of the line.
-                    end_offset = len(line.rstrip())
-
-                # show indicators if primary char doesn't span the frame line
-                if end_offset - start_offset < len(stripped_line) or (
-                        anchors and anchors.right_start_offset - anchors.left_end_offset > 0):
-                    # When showing this on a terminal, some of the non-ASCII characters
-                    # might be rendered as double-width characters, so we need to take
-                    # that into account when calculating the length of the line.
-                    dp_start_offset = _display_width(line, start_offset) + 1
-                    dp_end_offset = _display_width(line, end_offset) + 1
-
-                    row.append('    ')
-                    row.append(' ' * (dp_start_offset - stripped_characters))
-
-                    if anchors:
-                        dp_left_end_offset = _display_width(code_segment, anchors.left_end_offset)
-                        dp_right_start_offset = _display_width(code_segment, anchors.right_start_offset)
-                        row.append(anchors.primary_char * dp_left_end_offset)
-                        row.append(anchors.secondary_char * (dp_right_start_offset - dp_left_end_offset))
-                        row.append(anchors.primary_char * (dp_end_offset - dp_start_offset - dp_right_start_offset))
-                    else:
-                        row.append('^' * (dp_end_offset - dp_start_offset))
+                with suppress(Exception):
+                    anchors = _extract_caret_anchors_from_line_segment(segment)
+
+                # only use carets if there are anchors or the carets do not span all lines
+                show_carets = False
+                if anchors or all_lines[0][:start_offset].lstrip() or all_lines[-1][end_offset:].rstrip():
+                    show_carets = True
+
+                result = []
+
+                # only display first line, last line, and lines around anchor start/end
+                significant_lines = {0, len(all_lines) - 1}
+
+                anchors_left_end_offset = 0
+                anchors_right_start_offset = 0
+                primary_char = "^"
+                secondary_char = "^"
+                if anchors:
+                    anchors_left_end_offset = anchors.left_end_offset
+                    anchors_right_start_offset = anchors.right_start_offset
+                    # computed anchor positions do not take start_offset into account,
+                    # so account for it here
+                    if anchors.left_end_lineno == 0:
+                        anchors_left_end_offset += start_offset
+                    if anchors.right_start_lineno == 0:
+                        anchors_right_start_offset += start_offset
+
+                    # account for display width
+                    anchors_left_end_offset = _display_width(
+                        all_lines[anchors.left_end_lineno], offset=anchors_left_end_offset
+                    )
+                    anchors_right_start_offset = _display_width(
+                        all_lines[anchors.right_start_lineno], offset=anchors_right_start_offset
+                    )
 
-                    row.append('\n')
+                    primary_char = anchors.primary_char
+                    secondary_char = anchors.secondary_char
+                    significant_lines.update(
+                        range(anchors.left_end_lineno - 1, anchors.left_end_lineno + 2)
+                    )
+                    significant_lines.update(
+                        range(anchors.right_start_lineno - 1, anchors.right_start_lineno + 2)
+                    )
 
+                # remove bad line numbers
+                significant_lines.discard(-1)
+                significant_lines.discard(len(all_lines))
+
+                def output_line(lineno):
+                    """output all_lines[lineno] along with carets"""
+                    result.append(all_lines[lineno] + "\n")
+                    if not show_carets:
+                        return
+                    num_spaces = len(all_lines[lineno]) - len(all_lines[lineno].lstrip())
+                    carets = []
+                    num_carets = dp_end_offset if lineno == len(all_lines) - 1 else _display_width(all_lines[lineno])
+                    # compute caret character for each position
+                    for col in range(num_carets):
+                        if col < num_spaces or (lineno == 0 and col < dp_start_offset):
+                            # before first non-ws char of the line, or before start of instruction
+                            carets.append(' ')
+                        elif anchors and (
+                            lineno > anchors.left_end_lineno or
+                            (lineno == anchors.left_end_lineno and col >= anchors_left_end_offset)
+                        ) and (
+                            lineno < anchors.right_start_lineno or
+                            (lineno == anchors.right_start_lineno and col < anchors_right_start_offset)
+                        ):
+                            # within anchors
+                            carets.append(secondary_char)
+                        else:
+                            carets.append(primary_char)
+                    result.append("".join(carets) + "\n")
+
+                # display significant lines
+                sig_lines_list = sorted(significant_lines)
+                for i, lineno in enumerate(sig_lines_list):
+                    if i:
+                        linediff = lineno - sig_lines_list[i - 1]
+                        if linediff == 2:
+                            # 1 line in between - just output it
+                            output_line(lineno - 1)
+                        elif linediff > 2:
+                            # > 1 line in between - abbreviate
+                            result.append(f"...<{linediff - 1} lines>...\n")
+                    output_line(lineno)
+
+                row.append(
+                    textwrap.indent(textwrap.dedent("".join(result)), '    ', lambda line: True)
+                )
         if frame_summary.locals:
             for name, value in sorted(frame_summary.locals.items()):
                 row.append('    {name} = {value}\n'.format(name=name, value=value))
@@ -599,7 +699,9 @@ def _byte_offset_to_character_offset(str, offset):
 _Anchors = collections.namedtuple(
     "_Anchors",
     [
+        "left_end_lineno",
         "left_end_offset",
+        "right_start_lineno",
         "right_start_offset",
         "primary_char",
         "secondary_char",
@@ -608,59 +710,161 @@ def _byte_offset_to_character_offset(str, offset):
 )
 
 def _extract_caret_anchors_from_line_segment(segment):
+    """
+    Given source code `segment` corresponding to a FrameSummary, determine:
+        - for binary ops, the location of the binary op
+        - for indexing and function calls, the location of the brackets.
+    `segment` is expected to be a valid Python expression.
+    """
     import ast
 
     try:
-        tree = ast.parse(segment)
+        # Without parentheses, `segment` is parsed as a statement.
+        # Binary ops, subscripts, and calls are expressions, so
+        # we can wrap them with parentheses to parse them as
+        # (possibly multi-line) expressions.
+        # e.g. if we try to highlight the addition in
+        # x = (
+        #     a +
+        #     b
+        # )
+        # then we would ast.parse
+        #     a +
+        #     b
+        # which is not a valid statement because of the newline.
+        # Adding brackets makes it a valid expression.
+        # (
+        #     a +
+        #     b
+        # )
+        # Line locations will be different than the original,
+        # which is taken into account later on.
+        tree = ast.parse(f"(\n{segment}\n)")
     except SyntaxError:
         return None
 
     if len(tree.body) != 1:
         return None
 
-    normalize = lambda offset: _byte_offset_to_character_offset(segment, offset)
+    lines = segment.splitlines()
+
+    def normalize(lineno, offset):
+        """Get character index given byte offset"""
+        return _byte_offset_to_character_offset(lines[lineno], offset)
+
+    def next_valid_char(lineno, col):
+        """Gets the next valid character index in `lines`, if
+        the current location is not valid. Handles empty lines.
+        """
+        while lineno < len(lines) and col >= len(lines[lineno]):
+            col = 0
+            lineno += 1
+        assert lineno < len(lines) and col < len(lines[lineno])
+        return lineno, col
+
+    def increment(lineno, col):
+        """Get the next valid character index in `lines`."""
+        col += 1
+        lineno, col = next_valid_char(lineno, col)
+        return lineno, col
+
+    def nextline(lineno, col):
+        """Get the next valid character at least on the next line"""
+        col = 0
+        lineno += 1
+        lineno, col = next_valid_char(lineno, col)
+        return lineno, col
+
+    def increment_until(lineno, col, stop):
+        """Get the next valid non-"\\#" character that satisfies the `stop` predicate"""
+        while True:
+            ch = lines[lineno][col]
+            if ch in "\\#":
+                lineno, col = nextline(lineno, col)
+            elif not stop(ch):
+                lineno, col = increment(lineno, col)
+            else:
+                break
+        return lineno, col
+
+    def setup_positions(expr, force_valid=True):
+        """Get the lineno/col position of the end of `expr`. If `force_valid` is True,
+        forces the position to be a valid character (e.g. if the position is beyond the
+        end of the line, move to the next line)
+        """
+        # -2 since end_lineno is 1-indexed and because we added an extra
+        # bracket + newline to `segment` when calling ast.parse
+        lineno = expr.end_lineno - 2
+        col = normalize(lineno, expr.end_col_offset)
+        return next_valid_char(lineno, col) if force_valid else (lineno, col)
+
     statement = tree.body[0]
     match statement:
         case ast.Expr(expr):
             match expr:
                 case ast.BinOp():
-                    operator_start = normalize(expr.left.end_col_offset)
-                    operator_end = normalize(expr.right.col_offset)
-                    operator_str = segment[operator_start:operator_end]
-                    operator_offset = len(operator_str) - len(operator_str.lstrip())
+                    # ast gives these locations for BinOp subexpressions
+                    # ( left_expr ) + ( right_expr )
+                    #   left^^^^^       right^^^^^
+                    lineno, col = setup_positions(expr.left)
 
-                    left_anchor = expr.left.end_col_offset + operator_offset
-                    right_anchor = left_anchor + 1
+                    # First operator character is the first non-space/')' character
+                    lineno, col = increment_until(lineno, col, lambda x: not x.isspace() and x != ')')
+
+                    # binary op is 1 or 2 characters long, on the same line,
+                    # before the right subexpression
+                    right_col = col + 1
                     if (
-                        operator_offset + 1 < len(operator_str)
-                        and not operator_str[operator_offset + 1].isspace()
+                        right_col < len(lines[lineno])
+                        and (
+                            # operator char should not be in the right subexpression
+                            expr.right.lineno - 2 > lineno or
+                            right_col < normalize(expr.right.lineno - 2, expr.right.col_offset)
+                        )
+                        and not (ch := lines[lineno][right_col]).isspace()
+                        and ch not in "\\#"
                     ):
-                        right_anchor += 1
+                        right_col += 1
 
-                    while left_anchor < len(segment) and ((ch := segment[left_anchor]).isspace() or ch in ")#"):
-                        left_anchor += 1
-                        right_anchor += 1
-                    return _Anchors(normalize(left_anchor), normalize(right_anchor))
+                    # right_col can be invalid since it is exclusive
+                    return _Anchors(lineno, col, lineno, right_col)
                 case ast.Subscript():
-                    left_anchor = normalize(expr.value.end_col_offset)
-                    right_anchor = normalize(expr.slice.end_col_offset + 1)
-                    while left_anchor < len(segment) and ((ch := segment[left_anchor]).isspace() or ch != "["):
-                        left_anchor += 1
-                    while right_anchor < len(segment) and ((ch := segment[right_anchor]).isspace() or ch != "]"):
-                        right_anchor += 1
-                    if right_anchor < len(segment):
-                        right_anchor += 1
-                    return _Anchors(left_anchor, right_anchor)
+                    # ast gives these locations for value and slice subexpressions
+                    # ( value_expr ) [ slice_expr ]
+                    #   value^^^^^     slice^^^^^
+                    # subscript^^^^^^^^^^^^^^^^^^^^
+
+                    # find left bracket
+                    left_lineno, left_col = setup_positions(expr.value)
+                    left_lineno, left_col = increment_until(left_lineno, left_col, lambda x: x == '[')
+                    # find right bracket (final character of expression)
+                    right_lineno, right_col = setup_positions(expr, force_valid=False)
+                    return _Anchors(left_lineno, left_col, right_lineno, right_col)
+                case ast.Call():
+                    # ast gives these locations for function call expressions
+                    # ( func_expr ) (args, kwargs)
+                    #   func^^^^^
+                    # call^^^^^^^^^^^^^^^^^^^^^^^^
+
+                    # find left bracket
+                    left_lineno, left_col = setup_positions(expr.func)
+                    left_lineno, left_col = increment_until(left_lineno, left_col, lambda x: x == '(')
+                    # find right bracket (final character of expression)
+                    right_lineno, right_col = setup_positions(expr, force_valid=False)
+                    return _Anchors(left_lineno, left_col, right_lineno, right_col)
 
     return None
 
 _WIDE_CHAR_SPECIFIERS = "WF"
 
-def _display_width(line, offset):
+def _display_width(line, offset=None):
     """Calculate the extra amount of width space the given source
     code segment might take if it were to be displayed on a fixed
     width output device. Supports wide unicode characters and emojis."""
 
+    if offset is None:
+        offset = len(line)
+
     # Fast track for ASCII-only strings
     if line.isascii():
         return offset
diff --git a/Misc/NEWS.d/next/Library/2023-11-15-01-36-04.gh-issue-106922.qslOVH.rst b/Misc/NEWS.d/next/Library/2023-11-15-01-36-04.gh-issue-106922.qslOVH.rst
new file mode 100644
index 00000000000000..b68e75ab87cd0b
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2023-11-15-01-36-04.gh-issue-106922.qslOVH.rst
@@ -0,0 +1 @@
+Display multiple lines with ``traceback`` when errors span multiple lines.

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