diff --git a/changelog/14814.bugfix.rst b/changelog/14814.bugfix.rst
new file mode 100644
index 00000000000..6e44ab4976f
--- /dev/null
+++ b/changelog/14814.bugfix.rst
@@ -0,0 +1 @@
+Fixed assertion rewriting evaluating a walrus operator (``:=``) or a starred argument out of order when a later argument assigned to the same name, so ``assert collect(*items, identity(items := [9]))`` now passes the pre-assignment ``items``.
diff --git a/changelog/14815.improvement.rst b/changelog/14815.improvement.rst
new file mode 100644
index 00000000000..0e316edea07
--- /dev/null
+++ b/changelog/14815.improvement.rst
@@ -0,0 +1,4 @@
+Assertion failure messages now decompose subscript expressions, showing the container and the key that produced a value::
+
+    assert 1 == 99
+     +  where 1 = {'a': 1, 'b': 2}['a']
diff --git a/changelog/14816.improvement.rst b/changelog/14816.improvement.rst
new file mode 100644
index 00000000000..ca3ba124728
--- /dev/null
+++ b/changelog/14816.improvement.rst
@@ -0,0 +1,4 @@
+Assertion failure messages now show the condition of a conditional expression::
+
+    assert 0 == 99
+     +  where 0 = (... if True else ...)
diff --git a/src/_pytest/assertion/rewrite.py b/src/_pytest/assertion/rewrite.py
index 27953336c5c..27d9285aa82 100644
--- a/src/_pytest/assertion/rewrite.py
+++ b/src/_pytest/assertion/rewrite.py
@@ -967,19 +967,40 @@ def visit_operand(
         """Visit an operand, freezing it against walrus operators in *later*.
 
         Operands are rewritten into statements that run in source order, but
-        a plain name is left as a bare load evaluated at the very end, when
-        the enclosing expression is assembled.  A walrus operator in a later
-        operand rebinds that name in between, so both the value used and the
-        value reported would be the post-walrus one -- Python evaluates the
-        earlier operand first.  Copy the value into a temporary instead.
+        two of them stay unhoisted and are evaluated at the very end, when the
+        enclosing expression is assembled -- after everything that follows
+        them:
+
+        * a plain name, which a walrus operator in a later operand rebinds in
+          between, so the value used and the value reported would be the
+          post-walrus one;
+        * a walrus operator itself, which would then assign in the wrong
+          order, and be visible to the operands that were meant to precede it.
+
+        Either way Python evaluates the earlier operand first, so copy it into
+        a temporary here.  A starred argument is unwrapped and rewrapped, its
+        value being subject to the same problem.
         """
         specifiers = set(self.explanation_specifiers)
         res, expl = self.visit(operand)
-        if isinstance(res, ast.Name) and res.id in _walrus_targets(later):
-            snapshot = self.assign(res)
+        value = res.value if isinstance(res, ast.Starred) else res
+        if isinstance(value, ast.NamedExpr):
+            needs_freeze = bool(later)
+        else:
+            # Every other operand arrives as a temporary: the visit_* methods
+            # hoist what they build, and generic_visit assigns whatever is left
+            # -- a literal included -- so a name is all that can reach here.
+            assert isinstance(value, ast.Name)
+            needs_freeze = value.id in _walrus_targets(later)
+        if needs_freeze:
+            snapshot = self.assign(value)
             for key in set(self.explanation_specifiers) - specifiers:
                 self.explanation_specifiers[key] = self.display(snapshot)
-            res = snapshot
+            res = (
+                ast.copy_location(ast.Starred(snapshot, res.ctx), res)
+                if isinstance(res, ast.Starred)
+                else snapshot
+            )
         return res, expl
 
     def visit_BoolOp(self, boolop: ast.BoolOp) -> tuple[ast.Name, str]:
@@ -1088,9 +1109,36 @@ def visit_Starred(self, starred: ast.Starred) -> tuple[ast.Starred, str]:
         new_starred = ast.Starred(res, starred.ctx)
         return new_starred, "*" + expl
 
+    def visit_IfExp(self, ifexp: ast.IfExp) -> tuple[ast.Name, str]:
+        # Introspect the condition but keep the branches as they are: only the
+        # selected one may be evaluated, so neither can be hoisted.  That also
+        # keeps them ordered after the condition, which is where Python puts
+        # them, so no freeze is needed here.
+        cond_res, cond_expl = self.visit(ifexp.test)
+        res = self.assign(
+            ast.copy_location(ast.IfExp(cond_res, ifexp.body, ifexp.orelse), ifexp)
+        )
+        res_expl = self.explanation_param(self.display(res))
+        pat = "%s\n{%s = (... if %s else ...)\n}"
+        expl = pat % (res_expl, res_expl, cond_expl)
+        return res, expl
+
+    def visit_Subscript(self, subscript: ast.Subscript) -> tuple[ast.Name, str]:
+        # For Slice objects (a[1:3]), fall back to generic — decomposing
+        # start/stop/step is rarely useful in assertion messages.
+        if isinstance(subscript.slice, ast.Slice):
+            return self.generic_visit(subscript)
+        value, value_expl = self.visit_operand(subscript.value, [subscript.slice])
+        slice_res, slice_expl = self.visit(subscript.slice)
+        res = self.assign(
+            ast.copy_location(ast.Subscript(value, slice_res, ast.Load()), subscript)
+        )
+        res_expl = self.explanation_param(self.display(res))
+        pat = "%s\n{%s = %s[%s]\n}"
+        expl = pat % (res_expl, res_expl, value_expl, slice_expl)
+        return res, expl
+
     def visit_Attribute(self, attr: ast.Attribute) -> tuple[ast.Name, str]:
-        if not isinstance(attr.ctx, ast.Load):
-            return self.generic_visit(attr)
         value, value_expl = self.visit(attr.value)
         res = self.assign(
             ast.copy_location(ast.Attribute(value, attr.attr, ast.Load()), attr)
@@ -1105,8 +1153,6 @@ def visit_Compare(self, comp: ast.Compare) -> tuple[ast.expr, str]:
         left_res, left_expl = self.visit_operand(comp.left, comp.comparators)
         if isinstance(comp.left, ast.Compare | ast.BoolOp):
             left_expl = f"({left_expl})"
-        if isinstance(left_res, ast.NamedExpr):
-            left_res = self.assign(left_res)
         res_variables = [self.variable() for i in range(len(comp.ops))]
         load_names: list[ast.expr] = [ast.Name(v, ast.Load()) for v in res_variables]
         store_names = [ast.Name(v, ast.Store()) for v in res_variables]
diff --git a/testing/test_assertrewrite_coverage.py b/testing/test_assertrewrite_coverage.py
index 43a3f668f73..8af2a741c23 100644
--- a/testing/test_assertrewrite_coverage.py
+++ b/testing/test_assertrewrite_coverage.py
@@ -535,6 +535,26 @@ def check():
 class TestIntrospectionSubscript:
     """Subscript / indexing."""
 
+    def test_dict_subscript_shows_key_and_container(self) -> None:
+        assert_introspects(
+            """
+            def check():
+                d = {"a": 1, "b": 2}
+                assert d["a"] == 99
+            """,
+            must_contain=["where 1 = ", "['a']"],
+        )
+
+    def test_list_subscript_shows_index_and_container(self) -> None:
+        assert_introspects(
+            """
+            def check():
+                items = [10, 20, 30]
+                assert items[1] == 99
+            """,
+            must_contain=["where 20 = ", "[1]"],
+        )
+
     def test_subscript_semantics_preserved(self) -> None:
         assert_semantically_equivalent("""
             def check():
@@ -557,6 +577,16 @@ def check():
 class TestIntrospectionIfExp:
     """Ternary / if-expression."""
 
+    def test_ifexp_shows_condition_value(self) -> None:
+        assert_introspects(
+            """
+            def check():
+                flag = True
+                assert (0 if flag else 1) == 1
+            """,
+            must_contain=["if True else"],
+        )
+
     def test_ifexp_semantics_preserved(self) -> None:
         assert_semantically_equivalent("""
             def check():
@@ -564,6 +594,16 @@ def check():
                 assert (0 if flag else 1) == 1
             """)
 
+    def test_ifexp_in_compare_shows_result(self) -> None:
+        assert_introspects(
+            """
+            def check():
+                flag = True
+                assert (0 if flag else 1) == 99
+            """,
+            must_contain=["assert 0 == 99", "if True else"],
+        )
+
     def test_ifexp_short_circuit_true(self) -> None:
         """Orelse branch must NOT be evaluated when condition is True."""
         assert_passes_when_true("""
@@ -976,6 +1016,21 @@ def identity(v):
                 return "passed", value
             """)
 
+    def test_starred_argument_precedes_walrus(self) -> None:
+        assert_evaluation_order("""
+            def check():
+                def identity(v):
+                    return v
+                def collect(*values):
+                    return values
+                items = [1]
+                try:
+                    assert collect(*items, identity(items := [9])) == (1, [9])
+                except AssertionError:
+                    return "raised", items
+                return "passed", items
+            """)
+
     def test_chained_compare_operands_in_order(self) -> None:
         assert_evaluation_order("""
             def check():
@@ -989,6 +1044,21 @@ def identity(v):
                 return "passed", value
             """)
 
+    def test_bare_walrus_argument_in_order(self) -> None:
+        """A walrus argument is evaluated in place, before the ones after it."""
+        assert_evaluation_order("""
+            def check():
+                def identity(v):
+                    return v
+                def collect(*values):
+                    return values
+                try:
+                    assert collect((x := 1), identity(x := 2)) == (1, 2)
+                except AssertionError:
+                    return "raised", x
+                return "passed", x
+            """)
+
     def test_container_literal_operand_in_order(self) -> None:
         """Guard: ``generic_visit`` hoists container literals into a temporary."""
         assert_evaluation_order("""
@@ -1120,6 +1190,18 @@ def identity(v):
 class TestEdgeCases:
     """Regression and edge-case tests combining multiple expression types."""
 
+    def test_subscript_with_variable_key(self) -> None:
+        """Subscript where the key is a variable (not constant)."""
+        assert_introspects(
+            """
+            def check():
+                d = {"hello": 42}
+                key = "hello"
+                assert d[key] == 100
+            """,
+            must_contain=["where 42 = ", "['hello']"],
+        )
+
     def test_subscript_with_call_key(self) -> None:
         """Subscript where the key is a function call."""
         assert_introspects(
@@ -1160,6 +1242,18 @@ def __repr__(self):
             must_contain=["42", "100"],
         )
 
+    def test_ifexp_with_call_condition(self) -> None:
+        """IfExp where condition is a function call."""
+        assert_introspects(
+            """
+            def check():
+                def is_ready():
+                    return False
+                assert (1 if is_ready() else 0) == 1
+            """,
+            must_contain=["if False else"],
+        )
+
     def test_walrus_in_subscript(self) -> None:
         """Walrus operator used as subscript key."""
         assert_semantically_equivalent("""