diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py
index 8f12d268b0e5a..b5ef028af1450 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py
@@ -12,7 +12,7 @@
 assert (
     # Leading test value
     True  # Trailing test value same-line
-    # Trailing test value own-line 
+    # Trailing test value own-line
 ), "Some string"  # Trailing msg same-line
 # Trailing assert
 
@@ -23,8 +23,133 @@
 assert (
     # Leading test value
     True  # Trailing test value same-line
-    # Trailing test value own-line 
+    # Trailing test value own-line
 
     # Test dangler
 ), "Some string"  # Trailing msg same-line
 # Trailing assert
+
+def test():
+    assert {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    } == expected, (
+        "Not what we expected and the message is too long to fit ineeeeee one line"
+    )
+
+    assert {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    } == expected, (
+        "Not what we expected and the message is too long to fit in one lineeeee"
+    )
+
+    assert {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    } == expected, "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeee"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+    ), "Not what we expected and the message is too long to fit in one lin"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeeeee"
+
+    assert expected == {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    }, "Not what we expected and the message is too long to fit ineeeeee one line"
+
+    assert expected == {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    }, "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeeeeeeee"
+
+    assert (
+        expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lin"
+
+    assert (
+        expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeee"
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap
index 78163db003be0..2db923a1dfbe6 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap
@@ -18,7 +18,7 @@ assert (  # Dangle1
 assert (
     # Leading test value
     True  # Trailing test value same-line
-    # Trailing test value own-line 
+    # Trailing test value own-line
 ), "Some string"  # Trailing msg same-line
 # Trailing assert
 
@@ -29,11 +29,136 @@ assert (
 assert (
     # Leading test value
     True  # Trailing test value same-line
-    # Trailing test value own-line 
+    # Trailing test value own-line
 
     # Test dangler
 ), "Some string"  # Trailing msg same-line
 # Trailing assert
+
+def test():
+    assert {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    } == expected, (
+        "Not what we expected and the message is too long to fit ineeeeee one line"
+    )
+
+    assert {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    } == expected, (
+        "Not what we expected and the message is too long to fit in one lineeeee"
+    )
+
+    assert {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    } == expected, "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeee"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+    ), "Not what we expected and the message is too long to fit in one lin"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeeeee"
+
+    assert expected == {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    }, "Not what we expected and the message is too long to fit ineeeeee one line"
+
+    assert expected == {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    }, "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeeeeeeee"
+
+    assert (
+        expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lin"
+
+    assert (
+        expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeee"
 ```
 
 ## Output
@@ -66,7 +191,142 @@ assert (
     # Trailing test value own-line
     # Test dangler
 ), "Some string"  # Trailing msg same-line
+
+
 # Trailing assert
+
+def test():
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expected
+    ), "Not what we expected and the message is too long to fit ineeeeee one line"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expected
+    ), "Not what we expected and the message is too long to fit in one lineeeee"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expected
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeee"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+    ), "Not what we expected and the message is too long to fit in one lin"
+
+    assert (
+        {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+        == expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeeeee"
+
+    assert expected == {
+        key1: value1,
+        key2: value2,
+        key3: value3,
+        key4: value4,
+        key5: value5,
+        key6: value6,
+        key7: value7,
+        key8: value8,
+        key9: value9,
+    }, "Not what we expected and the message is too long to fit ineeeeee one line"
+
+    assert (
+        expected
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeeeeeeee"
+
+    assert (
+        expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lin"
+
+    assert (
+        expectedeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee
+        == {
+            key1: value1,
+            key2: value2,
+            key3: value3,
+            key4: value4,
+            key5: value5,
+            key6: value6,
+            key7: value7,
+            key8: value8,
+            key9: value9,
+        }
+    ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeee"
 ```