diff --git a/AUTHORS b/AUTHORS
index 27c0b3ac408..789bd53be80 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -267,6 +267,7 @@ Kevin J. Foley
 Kian Eliasi
 Kian-Meng Ang
 Kim Soo
+Kiril Klein
 Kodi B. Arfer
 Kojo Idrissa
 Kostis Anagnostopoulos
diff --git a/changelog/8998.bugfix.rst b/changelog/8998.bugfix.rst
new file mode 100644
index 00000000000..bd3e51f7fcc
--- /dev/null
+++ b/changelog/8998.bugfix.rst
@@ -0,0 +1,3 @@
+Assertion failures comparing very large strings, lists, or dataclasses no longer hang for a long time (sometimes minutes) while building the diff.
+
+When the inputs are large enough that :func:`difflib.ndiff` would be pathologically slow, pytest now falls back to a faster line-level diff and notes this in the output.
diff --git a/src/_pytest/assertion/_compare_sequence.py b/src/_pytest/assertion/_compare_sequence.py
index cd0043bf7ce..78976655d4f 100644
--- a/src/_pytest/assertion/_compare_sequence.py
+++ b/src/_pytest/assertion/_compare_sequence.py
@@ -6,6 +6,8 @@
 
 from _pytest._io.pprint import PrettyPrinter
 from _pytest._io.saferepr import saferepr
+from _pytest.assertion._diff import fast_unified_diff
+from _pytest.assertion._diff import ndiff_too_slow
 from _pytest.assertion._typing import _HighlightFunc
 from _pytest.compat import running_on_ci
 
@@ -27,6 +29,9 @@ def _compare_eq_iterable(
 
     yield ""
     yield "Full diff:"
+    if ndiff_too_slow(left_formatting, right_formatting):
+        yield from fast_unified_diff(left_formatting, right_formatting, highlighter)
+        return
     # "right" is the expected base against which we compare "left",
     # see https://github.com/pytest-dev/pytest/issues/3333
     yield from highlighter(
diff --git a/src/_pytest/assertion/_diff.py b/src/_pytest/assertion/_diff.py
new file mode 100644
index 00000000000..763dc48c918
--- /dev/null
+++ b/src/_pytest/assertion/_diff.py
@@ -0,0 +1,61 @@
+from __future__ import annotations
+
+from collections.abc import Iterator
+from collections.abc import Sequence
+
+from _pytest.assertion._typing import _HighlightFunc
+
+
+# Above this combined input size (in characters), ``difflib.ndiff`` becomes
+# pathologically slow: its character-level "fancy replace" step is quadratic in
+# the size of the differing region, so a few tens of kilobytes of differing text
+# can hang for minutes (see issue #8998).
+NDIFF_MAX_INPUT_SIZE = 10_000
+
+# Above this number of lines, both ``ndiff`` and ``unified_diff`` get slow,
+# since the underlying ``SequenceMatcher`` is quadratic in the number of lines
+# (a large nested structure can pretty-print to hundreds of thousands of lines).
+# We both fall back and cap the fallback's input at this many lines.
+DIFF_MAX_LINES = 1_000
+
+
+def ndiff_too_slow(left_lines: Sequence[str], right_lines: Sequence[str]) -> bool:
+    """Return True if ``difflib.ndiff`` would likely be pathologically slow."""
+    if len(left_lines) > DIFF_MAX_LINES or len(right_lines) > DIFF_MAX_LINES:
+        return True
+    size = sum(len(line) for line in left_lines) + sum(
+        len(line) for line in right_lines
+    )
+    return size > NDIFF_MAX_INPUT_SIZE
+
+
+def fast_unified_diff(
+    left_lines: Sequence[str],
+    right_lines: Sequence[str],
+    highlighter: _HighlightFunc,
+) -> Iterator[str]:
+    """Yield a fast, coarse line-level diff for inputs too large for ``ndiff``.
+
+    Unlike ``ndiff`` this does not produce character-level "?" guide lines, and
+    it only diffs the first ``DIFF_MAX_LINES`` lines of each side, but it
+    completes in milliseconds where ``ndiff`` would hang (see issue #8998).
+
+    "right" is the expected base against which we compare "left",
+    see https://github.com/pytest-dev/pytest/issues/3333.
+    """
+    from difflib import unified_diff
+
+    yield (
+        f"Diff too large to compute in full (over {NDIFF_MAX_INPUT_SIZE} "
+        "characters); showing a faster line-level diff instead:"
+    )
+    left = [line.rstrip("\n") for line in left_lines[:DIFF_MAX_LINES]]
+    right = [line.rstrip("\n") for line in right_lines[:DIFF_MAX_LINES]]
+    hidden = max(len(left_lines), len(right_lines)) - DIFF_MAX_LINES
+    if hidden > 0:
+        yield f"Diffing only the first {DIFF_MAX_LINES} lines; {hidden} more hidden"
+    diff = unified_diff(right, left, n=3, lineterm="")
+    # The first two lines are the always-empty "--- "/"+++ " file headers.
+    next(diff, None)
+    next(diff, None)
+    yield from highlighter("\n".join(diff), lexer="diff").splitlines()
diff --git a/src/_pytest/assertion/compare_text.py b/src/_pytest/assertion/compare_text.py
index 31096444ba6..92e9e209f69 100644
--- a/src/_pytest/assertion/compare_text.py
+++ b/src/_pytest/assertion/compare_text.py
@@ -3,6 +3,8 @@
 from collections.abc import Iterator
 
 from _pytest._io.saferepr import saferepr
+from _pytest.assertion._diff import fast_unified_diff
+from _pytest.assertion._diff import ndiff_too_slow
 from _pytest.assertion._typing import _AssertionTextDiffStyle
 from _pytest.assertion._typing import _HighlightFunc
 from _pytest.assertion.highlight import dummy_highlighter
@@ -75,13 +77,15 @@ def _diff_text(
         left = repr(str(left))
         right = repr(str(right))
         yield "Strings contain only whitespace, escaping them using repr()"
+    left_lines = left.splitlines(keepends)
+    right_lines = right.splitlines(keepends)
+    if ndiff_too_slow(left_lines, right_lines):
+        yield from fast_unified_diff(left_lines, right_lines, highlighter)
+        return
     # "right" is the expected base against which we compare "left",
     # see https://github.com/pytest-dev/pytest/issues/3333
     yield from highlighter(
-        "\n".join(
-            line.strip("\n")
-            for line in ndiff(right.splitlines(keepends), left.splitlines(keepends))
-        ),
+        "\n".join(line.strip("\n") for line in ndiff(right_lines, left_lines)),
         lexer="diff",
     ).splitlines()
 
diff --git a/testing/test_assertion.py b/testing/test_assertion.py
index c25487bdf33..79c576d9547 100644
--- a/testing/test_assertion.py
+++ b/testing/test_assertion.py
@@ -17,6 +17,7 @@
 from _pytest.assertion import truncate
 from _pytest.assertion import util
 from _pytest.assertion._compare_any import _compare_eq_cls
+from _pytest.assertion._diff import ndiff_too_slow
 from _pytest.assertion.compare_text import _compare_eq_text
 from _pytest.config import Config as _Config
 from _pytest.monkeypatch import MonkeyPatch
@@ -459,6 +460,19 @@ def callequal(
     )
 
 
+class TestNdiffTooSlow:
+    """Heuristic guarding against pathologically slow diffs (#8998)."""
+
+    def test_small_input_uses_ndiff(self) -> None:
+        assert ndiff_too_slow(["spam"], ["eggs"]) is False
+
+    def test_many_characters_is_too_slow(self) -> None:
+        assert ndiff_too_slow(["a" * 6000], ["b" * 6000]) is True
+
+    def test_many_lines_is_too_slow(self) -> None:
+        assert ndiff_too_slow(["x"] * 1001, ["y"]) is True
+
+
 class TestAssert_reprcompare:
     def test_different_types(self) -> None:
         assert callequal([0, 1], "foo") is None
@@ -513,6 +527,32 @@ def test_text_skipping_verbose(self) -> None:
         assert "- " + "a" * 50 + "eggs" in lines
         assert "+ " + "a" * 50 + "spam" in lines
 
+    def test_text_diff_large_input_skips_ndiff(self) -> None:
+        # A single huge differing line is above the character cutoff and falls
+        # back to a fast line-level diff instead of the pathologically slow
+        # ndiff (#8998).
+        left = "a" + "x" * 20000
+        right = "b" + "y" * 20000
+        lines = callequal(left, right, verbose=1)
+        assert lines is not None
+        assert any("Diff too large to compute in full" in line for line in lines)
+        # The character-level "?" guide lines produced by ndiff must not appear.
+        assert not any(line.startswith("? ") for line in lines)
+
+    def test_text_diff_many_lines_skips_ndiff(self) -> None:
+        # Many lines are above the line cutoff and fall back, capping the
+        # number of lines actually diffed (#8998).
+        left = "\n".join(f"left line {i}" for i in range(2000))
+        right = "\n".join(f"right line {i}" for i in range(2000))
+        lines = callequal(left, right, verbose=1)
+        assert lines is not None
+        assert any("Diff too large to compute in full" in line for line in lines)
+        assert any("Diffing only the first 1000 lines" in line for line in lines)
+        assert not any(line.startswith("? ") for line in lines)
+        # The fallback still shows which lines differ.
+        assert "-right line 0" in lines
+        assert "+left line 0" in lines
+
     def test_multiline_text_diff(self) -> None:
         left = "foo\nspam\nbar"
         right = "foo\neggs\nbar"
@@ -673,6 +713,17 @@ def test_iterable_quiet(self) -> None:
             "Use -v to get more diff",
         ]
 
+    def test_iterable_large_input_skips_ndiff(self) -> None:
+        # Large iterables fall back to a fast line-level diff instead of the
+        # pathologically slow ndiff over their pprint output (#8998).
+        left = [f"item-{i}" for i in range(2000)]
+        right = [f"other-{i}" for i in range(2000)]
+        lines = callequal(left, right, verbose=1)
+        assert lines is not None
+        assert "Full diff:" in lines
+        assert any("Diff too large to compute in full" in line for line in lines)
+        assert not any(line.startswith("? ") for line in lines)
+
     def test_iterable_full_diff_ci(
         self, monkeypatch: MonkeyPatch, pytester: Pytester
     ) -> None: