diff --git a/AUTHORS b/AUTHORS
index 0395feceb..448b71d3a 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -12,6 +12,7 @@ Adam Uhlir
 Ahn Ki-Wook
 Akiomi Kamakura
 Alan Velasco
+Alessio Izzo
 Alexander Johnson
 Alexander King
 Alexei Kozlenok
diff --git a/changelog/10743.bugfix.rst b/changelog/10743.bugfix.rst
new file mode 100644
index 000000000..ad5c63e80
--- /dev/null
+++ b/changelog/10743.bugfix.rst
@@ -0,0 +1 @@
+The assertion rewriting mechanism now works correctly when assertion expressions contain the walrus operator.
diff --git a/src/_pytest/assertion/rewrite.py b/src/_pytest/assertion/rewrite.py
index 42664add4..8b1823470 100644
--- a/src/_pytest/assertion/rewrite.py
+++ b/src/_pytest/assertion/rewrite.py
@@ -44,10 +44,14 @@ from _pytest.stash import StashKey
 if TYPE_CHECKING:
     from _pytest.assertion import AssertionState
 
+if sys.version_info >= (3, 8):
+    namedExpr = ast.NamedExpr
+else:
+    namedExpr = ast.Expr
+
 
 assertstate_key = StashKey["AssertionState"]()
 
-
 # pytest caches rewritten pycs in pycache dirs
 PYTEST_TAG = f"{sys.implementation.cache_tag}-pytest-{version}"
 PYC_EXT = ".py" + (__debug__ and "c" or "o")
@@ -635,8 +639,12 @@ class AssertionRewriter(ast.NodeVisitor):
        .push_format_context() and .pop_format_context() which allows
        to build another %-formatted string while already building one.
 
-    This state is reset on every new assert statement visited and used
-    by the other visitors.
+    :variables_overwrite: A dict filled with references to variables
+       that change value within an assert. This happens when a variable is
+       reassigned with the walrus operator
+
+    This state, except the variables_overwrite,  is reset on every new assert
+    statement visited and used by the other visitors.
     """
 
     def __init__(
@@ -652,6 +660,7 @@ class AssertionRewriter(ast.NodeVisitor):
         else:
             self.enable_assertion_pass_hook = False
         self.source = source
+        self.variables_overwrite: Dict[str, str] = {}
 
     def run(self, mod: ast.Module) -> None:
         """Find all assert statements in *mod* and rewrite them."""
@@ -666,7 +675,7 @@ class AssertionRewriter(ast.NodeVisitor):
         if doc is not None and self.is_rewrite_disabled(doc):
             return
         pos = 0
-        lineno = 1
+        item = None
         for item in mod.body:
             if (
                 expect_docstring
@@ -937,6 +946,18 @@ class AssertionRewriter(ast.NodeVisitor):
                 ast.copy_location(node, assert_)
         return self.statements
 
+    def visit_NamedExpr(self, name: namedExpr) -> Tuple[namedExpr, str]:
+        # This method handles the 'walrus operator' repr of the target
+        # name if it's a local variable or _should_repr_global_name()
+        # thinks it's acceptable.
+        locs = ast.Call(self.builtin("locals"), [], [])
+        target_id = name.target.id  # type: ignore[attr-defined]
+        inlocs = ast.Compare(ast.Str(target_id), [ast.In()], [locs])
+        dorepr = self.helper("_should_repr_global_name", name)
+        test = ast.BoolOp(ast.Or(), [inlocs, dorepr])
+        expr = ast.IfExp(test, self.display(name), ast.Str(target_id))
+        return name, self.explanation_param(expr)
+
     def visit_Name(self, name: ast.Name) -> Tuple[ast.Name, str]:
         # Display the repr of the name if it's a local variable or
         # _should_repr_global_name() thinks it's acceptable.
@@ -963,6 +984,20 @@ class AssertionRewriter(ast.NodeVisitor):
                 # cond is set in a prior loop iteration below
                 self.expl_stmts.append(ast.If(cond, fail_inner, []))  # noqa
                 self.expl_stmts = fail_inner
+                # Check if the left operand is a namedExpr and the value has already been visited
+                if (
+                    isinstance(v, ast.Compare)
+                    and isinstance(v.left, namedExpr)
+                    and v.left.target.id
+                    in [
+                        ast_expr.id
+                        for ast_expr in boolop.values[:i]
+                        if hasattr(ast_expr, "id")
+                    ]
+                ):
+                    pytest_temp = self.variable()
+                    self.variables_overwrite[v.left.target.id] = pytest_temp
+                    v.left.target.id = pytest_temp
             self.push_format_context()
             res, expl = self.visit(v)
             body.append(ast.Assign([ast.Name(res_var, ast.Store())], res))
@@ -1038,6 +1073,9 @@ class AssertionRewriter(ast.NodeVisitor):
 
     def visit_Compare(self, comp: ast.Compare) -> Tuple[ast.expr, str]:
         self.push_format_context()
+        # We first check if we have overwritten a variable in the previous assert
+        if isinstance(comp.left, ast.Name) and comp.left.id in self.variables_overwrite:
+            comp.left.id = self.variables_overwrite[comp.left.id]
         left_res, left_expl = self.visit(comp.left)
         if isinstance(comp.left, (ast.Compare, ast.BoolOp)):
             left_expl = f"({left_expl})"
@@ -1049,6 +1087,13 @@ class AssertionRewriter(ast.NodeVisitor):
         syms = []
         results = [left_res]
         for i, op, next_operand in it:
+            if (
+                isinstance(next_operand, namedExpr)
+                and isinstance(left_res, ast.Name)
+                and next_operand.target.id == left_res.id
+            ):
+                next_operand.target.id = self.variable()
+                self.variables_overwrite[left_res.id] = next_operand.target.id
             next_res, next_expl = self.visit(next_operand)
             if isinstance(next_operand, (ast.Compare, ast.BoolOp)):
                 next_expl = f"({next_expl})"
@@ -1072,6 +1117,7 @@ class AssertionRewriter(ast.NodeVisitor):
             res: ast.expr = ast.BoolOp(ast.And(), load_names)
         else:
             res = load_names[0]
+
         return res, self.explanation_param(self.pop_format_context(expl_call))
 
 
diff --git a/testing/test_assertrewrite.py b/testing/test_assertrewrite.py
index 3c98392ed..8d9441403 100644
--- a/testing/test_assertrewrite.py
+++ b/testing/test_assertrewrite.py
@@ -1265,6 +1265,177 @@ class TestIssue2121:
         result.stdout.fnmatch_lines(["*E*assert (1 + 1) == 3"])
 
 
+@pytest.mark.skipif(
+    sys.version_info < (3, 8), reason="walrus operator not available in py<38"
+)
+class TestIssue10743:
+    def test_assertion_walrus_operator(self, pytester: Pytester) -> None:
+        pytester.makepyfile(
+            """
+            def my_func(before, after):
+                return before == after
+
+            def change_value(value):
+                return value.lower()
+
+            def test_walrus_conversion():
+                a = "Hello"
+                assert not my_func(a, a := change_value(a))
+                assert a == "hello"
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+    def test_assertion_walrus_operator_dont_rewrite(self, pytester: Pytester) -> None:
+        pytester.makepyfile(
+            """
+            'PYTEST_DONT_REWRITE'
+            def my_func(before, after):
+                return before == after
+
+            def change_value(value):
+                return value.lower()
+
+            def test_walrus_conversion_dont_rewrite():
+                a = "Hello"
+                assert not my_func(a, a := change_value(a))
+                assert a == "hello"
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+    def test_assertion_inline_walrus_operator(self, pytester: Pytester) -> None:
+        pytester.makepyfile(
+            """
+            def my_func(before, after):
+                return before == after
+
+            def test_walrus_conversion_inline():
+                a = "Hello"
+                assert not my_func(a, a := a.lower())
+                assert a == "hello"
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+    def test_assertion_inline_walrus_operator_reverse(self, pytester: Pytester) -> None:
+        pytester.makepyfile(
+            """
+            def my_func(before, after):
+                return before == after
+
+            def test_walrus_conversion_reverse():
+                a = "Hello"
+                assert my_func(a := a.lower(), a)
+                assert a == 'hello'
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+    def test_assertion_walrus_no_variable_name_conflict(
+        self, pytester: Pytester
+    ) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_conversion_no_conflict():
+                a = "Hello"
+                assert a == (b := a.lower())
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 1
+        result.stdout.fnmatch_lines(["*AssertionError: assert 'Hello' == 'hello'"])
+
+    def test_assertion_walrus_operator_true_assertion_and_changes_variable_value(
+        self, pytester: Pytester
+    ) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_conversion_succeed():
+                a = "Hello"
+                assert a != (a := a.lower())
+                assert a == 'hello'
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+    def test_assertion_walrus_operator_fail_assertion(self, pytester: Pytester) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_conversion_fails():
+                a = "Hello"
+                assert a == (a := a.lower())
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 1
+        result.stdout.fnmatch_lines(["*AssertionError: assert 'Hello' == 'hello'"])
+
+    def test_assertion_walrus_operator_boolean_composite(
+        self, pytester: Pytester
+    ) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_operator_change_boolean_value():
+                a = True
+                assert a and True and ((a := False) is False) and (a is False) and ((a := None) is None)
+                assert a is None
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+    def test_assertion_walrus_operator_compare_boolean_fails(
+        self, pytester: Pytester
+    ) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_operator_change_boolean_value():
+                a = True
+                assert not (a and ((a := False) is False))
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 1
+        result.stdout.fnmatch_lines(["*assert not (True and False is False)"])
+
+    def test_assertion_walrus_operator_boolean_none_fails(
+        self, pytester: Pytester
+    ) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_operator_change_boolean_value():
+                a = True
+                assert not (a and ((a := None) is None))
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 1
+        result.stdout.fnmatch_lines(["*assert not (True and None is None)"])
+
+    def test_assertion_walrus_operator_value_changes_cleared_after_each_test(
+        self, pytester: Pytester
+    ) -> None:
+        pytester.makepyfile(
+            """
+            def test_walrus_operator_change_value():
+                a = True
+                assert (a := None) is None
+
+            def test_walrus_operator_not_override_value():
+                a = True
+                assert a is True
+        """
+        )
+        result = pytester.runpytest()
+        assert result.ret == 0
+
+
 @pytest.mark.skipif(
     sys.maxsize <= (2**31 - 1), reason="Causes OverflowError on 32bit systems"
 )