diff --git a/changelog/4978.bugfix.rst b/changelog/4978.bugfix.rst
new file mode 100644
index 000000000..259daa8da
--- /dev/null
+++ b/changelog/4978.bugfix.rst
@@ -0,0 +1 @@
+``outcomes.Exit`` is not swallowed in ``assertrepr_compare`` anymore.
diff --git a/src/_pytest/assertion/util.py b/src/_pytest/assertion/util.py
index c7a46cba0..ab01c314c 100644
--- a/src/_pytest/assertion/util.py
+++ b/src/_pytest/assertion/util.py
@@ -9,6 +9,7 @@ import six
 
 import _pytest._code
 from ..compat import Sequence
+from _pytest import outcomes
 from _pytest._io.saferepr import saferepr
 
 # The _reprcompare attribute on the util module is used by the new assertion
@@ -102,6 +103,38 @@ except NameError:
     basestring = str
 
 
+def issequence(x):
+    return isinstance(x, Sequence) and not isinstance(x, basestring)
+
+
+def istext(x):
+    return isinstance(x, basestring)
+
+
+def isdict(x):
+    return isinstance(x, dict)
+
+
+def isset(x):
+    return isinstance(x, (set, frozenset))
+
+
+def isdatacls(obj):
+    return getattr(obj, "__dataclass_fields__", None) is not None
+
+
+def isattrs(obj):
+    return getattr(obj, "__attrs_attrs__", None) is not None
+
+
+def isiterable(obj):
+    try:
+        iter(obj)
+        return not istext(obj)
+    except TypeError:
+        return False
+
+
 def assertrepr_compare(config, op, left, right):
     """Return specialised explanations for some operators/operands"""
     width = 80 - 15 - len(op) - 2  # 15 chars indentation, 1 space around op
@@ -110,31 +143,6 @@ def assertrepr_compare(config, op, left, right):
 
     summary = u"%s %s %s" % (ecu(left_repr), op, ecu(right_repr))
 
-    def issequence(x):
-        return isinstance(x, Sequence) and not isinstance(x, basestring)
-
-    def istext(x):
-        return isinstance(x, basestring)
-
-    def isdict(x):
-        return isinstance(x, dict)
-
-    def isset(x):
-        return isinstance(x, (set, frozenset))
-
-    def isdatacls(obj):
-        return getattr(obj, "__dataclass_fields__", None) is not None
-
-    def isattrs(obj):
-        return getattr(obj, "__attrs_attrs__", None) is not None
-
-    def isiterable(obj):
-        try:
-            iter(obj)
-            return not istext(obj)
-        except TypeError:
-            return False
-
     verbose = config.getoption("verbose")
     explanation = None
     try:
@@ -162,6 +170,8 @@ def assertrepr_compare(config, op, left, right):
         elif op == "not in":
             if istext(left) and istext(right):
                 explanation = _notin_text(left, right, verbose)
+    except outcomes.Exit:
+        raise
     except Exception:
         explanation = [
             u"(pytest_assertion plugin: representation of details failed.  "
diff --git a/testing/test_assertion.py b/testing/test_assertion.py
index e4fe56c6f..330b711af 100644
--- a/testing/test_assertion.py
+++ b/testing/test_assertion.py
@@ -11,6 +11,7 @@ import six
 
 import _pytest.assertion as plugin
 import pytest
+from _pytest import outcomes
 from _pytest.assertion import truncate
 from _pytest.assertion import util
 
@@ -1305,3 +1306,13 @@ def test_issue_1944(testdir):
         "AttributeError: 'Module' object has no attribute '_obj'"
         not in result.stdout.str()
     )
+
+
+def test_exit_from_assertrepr_compare(monkeypatch):
+    def raise_exit(obj):
+        outcomes.exit("Quitting debugger")
+
+    monkeypatch.setattr(util, "istext", raise_exit)
+
+    with pytest.raises(outcomes.Exit, match="Quitting debugger"):
+        callequal(1, 1)