diff --git a/mypy/server/update.py b/mypy/server/update.py
index cd2c415cfd2d..686068a4aad0 100644
--- a/mypy/server/update.py
+++ b/mypy/server/update.py
@@ -115,6 +115,7 @@
 from __future__ import annotations
 
 import os
+import re
 import sys
 import time
 from typing import Callable, NamedTuple, Sequence, Union
@@ -182,7 +183,7 @@ def __init__(self, result: BuildResult) -> None:
         # Merge in any root dependencies that may not have been loaded
         merge_dependencies(manager.load_fine_grained_deps(FAKE_ROOT_MODULE), self.deps)
         self.previous_targets_with_errors = manager.errors.targets()
-        self.previous_messages = result.errors[:]
+        self.previous_messages: list[str] = result.errors[:]
         # Module, if any, that had blocking errors in the last run as (id, path) tuple.
         self.blocking_error: tuple[str, str] | None = None
         # Module that we haven't processed yet but that are known to be stale.
@@ -290,6 +291,7 @@ def update(
                     messages = self.manager.errors.new_messages()
                     break
 
+        messages = sort_messages_preserving_file_order(messages, self.previous_messages)
         self.previous_messages = messages[:]
         return messages
 
@@ -1260,3 +1262,61 @@ def refresh_suppressed_submodules(
                                 state.suppressed.append(submodule)
                                 state.suppressed_set.add(submodule)
     return messages
+
+
+def extract_fnam_from_message(message: str) -> str | None:
+    m = re.match(r"([^:]+):[0-9]+: (error|note): ", message)
+    if m:
+        return m.group(1)
+    return None
+
+
+def extract_possible_fnam_from_message(message: str) -> str:
+    # This may return non-path things if there is some random colon on the line
+    return message.split(":", 1)[0]
+
+
+def sort_messages_preserving_file_order(
+    messages: list[str], prev_messages: list[str]
+) -> list[str]:
+    """Sort messages so that the order of files is preserved.
+
+    An update generates messages so that the files can be in a fairly
+    arbitrary order.  Preserve the order of files to avoid messages
+    getting reshuffled continuously.  If there are messages in
+    additional files, sort them towards the end.
+    """
+    # Calculate file order from the previous messages
+    n = 0
+    order = {}
+    for msg in prev_messages:
+        fnam = extract_fnam_from_message(msg)
+        if fnam and fnam not in order:
+            order[fnam] = n
+            n += 1
+
+    # Related messages must be sorted as a group of successive lines
+    groups = []
+    i = 0
+    while i < len(messages):
+        msg = messages[i]
+        maybe_fnam = extract_possible_fnam_from_message(msg)
+        group = [msg]
+        if maybe_fnam in order:
+            # This looks like a file name. Collect all lines related to this message.
+            while (
+                i + 1 < len(messages)
+                and extract_possible_fnam_from_message(messages[i + 1]) not in order
+                and extract_fnam_from_message(messages[i + 1]) is None
+                and not messages[i + 1].startswith("mypy: ")
+            ):
+                i += 1
+                group.append(messages[i])
+        groups.append((order.get(maybe_fnam, n), group))
+        i += 1
+
+    groups = sorted(groups, key=lambda g: g[0])
+    result = []
+    for key, group in groups:
+        result.extend(group)
+    return result
diff --git a/mypy/test/testfinegrained.py b/mypy/test/testfinegrained.py
index e797b4b7a35b..1fc73146e749 100644
--- a/mypy/test/testfinegrained.py
+++ b/mypy/test/testfinegrained.py
@@ -17,6 +17,7 @@
 import os
 import re
 import sys
+import unittest
 from typing import Any, cast
 
 import pytest
@@ -30,6 +31,7 @@
 from mypy.modulefinder import BuildSource
 from mypy.options import Options
 from mypy.server.mergecheck import check_consistency
+from mypy.server.update import sort_messages_preserving_file_order
 from mypy.test.config import test_temp_dir
 from mypy.test.data import DataDrivenTestCase, DataSuite, DeleteFile, UpdateFile
 from mypy.test.helpers import (
@@ -369,3 +371,70 @@ def get_inspect(self, program_text: str, incremental_step: int) -> list[tuple[st
 
 def normalize_messages(messages: list[str]) -> list[str]:
     return [re.sub("^tmp" + re.escape(os.sep), "", message) for message in messages]
+
+
+class TestMessageSorting(unittest.TestCase):
+    def test_simple_sorting(self) -> None:
+        msgs = ['x.py:1: error: "int" not callable', 'foo/y.py:123: note: "X" not defined']
+        old_msgs = ['foo/y.py:12: note: "Y" not defined', 'x.py:8: error: "str" not callable']
+        assert sort_messages_preserving_file_order(msgs, old_msgs) == list(reversed(msgs))
+        assert sort_messages_preserving_file_order(list(reversed(msgs)), old_msgs) == list(
+            reversed(msgs)
+        )
+
+    def test_long_form_sorting(self) -> None:
+        # Multi-line errors should be sorted together and not split.
+        msg1 = [
+            'x.py:1: error: "int" not callable',
+            "and message continues (x: y)",
+            "    1()",
+            "    ^~~",
+        ]
+        msg2 = [
+            'foo/y.py: In function "f":',
+            'foo/y.py:123: note: "X" not defined',
+            "and again message continues",
+        ]
+        old_msgs = ['foo/y.py:12: note: "Y" not defined', 'x.py:8: error: "str" not callable']
+        assert sort_messages_preserving_file_order(msg1 + msg2, old_msgs) == msg2 + msg1
+        assert sort_messages_preserving_file_order(msg2 + msg1, old_msgs) == msg2 + msg1
+
+    def test_mypy_error_prefix(self) -> None:
+        # Some errors don't have a file and start with "mypy: ". These
+        # shouldn't be sorted together with file-specific errors.
+        msg1 = 'x.py:1: error: "int" not callable'
+        msg2 = 'foo/y:123: note: "X" not defined'
+        msg3 = "mypy: Error not associated with a file"
+        old_msgs = [
+            "mypy: Something wrong",
+            'foo/y:12: note: "Y" not defined',
+            'x.py:8: error: "str" not callable',
+        ]
+        assert sort_messages_preserving_file_order([msg1, msg2, msg3], old_msgs) == [
+            msg2,
+            msg1,
+            msg3,
+        ]
+        assert sort_messages_preserving_file_order([msg3, msg2, msg1], old_msgs) == [
+            msg2,
+            msg1,
+            msg3,
+        ]
+
+    def test_new_file_at_the_end(self) -> None:
+        msg1 = 'x.py:1: error: "int" not callable'
+        msg2 = 'foo/y.py:123: note: "X" not defined'
+        new1 = "ab.py:3: error: Problem: error"
+        new2 = "aaa:3: error: Bad"
+        old_msgs = ['foo/y.py:12: note: "Y" not defined', 'x.py:8: error: "str" not callable']
+        assert sort_messages_preserving_file_order([msg1, msg2, new1], old_msgs) == [
+            msg2,
+            msg1,
+            new1,
+        ]
+        assert sort_messages_preserving_file_order([new1, msg1, msg2, new2], old_msgs) == [
+            msg2,
+            msg1,
+            new1,
+            new2,
+        ]
diff --git a/test-data/unit/fine-grained-blockers.test b/test-data/unit/fine-grained-blockers.test
index f3991c0d31e4..a134fb1d4301 100644
--- a/test-data/unit/fine-grained-blockers.test
+++ b/test-data/unit/fine-grained-blockers.test
@@ -317,8 +317,8 @@ a.py:1: error: invalid syntax
 ==
 a.py:1: error: invalid syntax
 ==
-b.py:3: error: Too many arguments for "f"
 a.py:3: error: Too many arguments for "g"
+b.py:3: error: Too many arguments for "f"
 
 [case testDeleteFileWithBlockingError-only_when_nocache]
 -- Different cache/no-cache tests because:
diff --git a/test-data/unit/fine-grained-follow-imports.test b/test-data/unit/fine-grained-follow-imports.test
index 4eb55fb125f7..ebe8b86b37ab 100644
--- a/test-data/unit/fine-grained-follow-imports.test
+++ b/test-data/unit/fine-grained-follow-imports.test
@@ -587,8 +587,8 @@ def f() -> None:
 main.py:2: error: Cannot find implementation or library stub for module named "p"
 main.py:2: note: See https://mypy.readthedocs.io/en/stable/running_mypy.html#missing-imports
 ==
-p/m.py:1: error: "str" not callable
 p/__init__.py:1: error: "int" not callable
+p/m.py:1: error: "str" not callable
 
 [case testFollowImportsNormalPackageInitFileStub]
 # flags: --follow-imports=normal
@@ -610,11 +610,11 @@ x x x
 main.py:1: error: Cannot find implementation or library stub for module named "p"
 main.py:1: note: See https://mypy.readthedocs.io/en/stable/running_mypy.html#missing-imports
 ==
-p/m.pyi:1: error: "str" not callable
 p/__init__.pyi:1: error: "int" not callable
-==
 p/m.pyi:1: error: "str" not callable
+==
 p/__init__.pyi:1: error: "int" not callable
+p/m.pyi:1: error: "str" not callable
 
 [case testFollowImportsNormalNamespacePackages]
 # flags: --follow-imports=normal --namespace-packages
@@ -638,12 +638,12 @@ main.py:2: error: Cannot find implementation or library stub for module named "p
 main.py:2: note: See https://mypy.readthedocs.io/en/stable/running_mypy.html#missing-imports
 main.py:2: error: Cannot find implementation or library stub for module named "p2"
 ==
-p2/m2.py:1: error: "str" not callable
 p1/m1.py:1: error: "int" not callable
+p2/m2.py:1: error: "str" not callable
 ==
+p1/m1.py:1: error: "int" not callable
 main.py:2: error: Cannot find implementation or library stub for module named "p2.m2"
 main.py:2: note: See https://mypy.readthedocs.io/en/stable/running_mypy.html#missing-imports
-p1/m1.py:1: error: "int" not callable
 
 [case testFollowImportsNormalNewFileOnCommandLine]
 # flags: --follow-imports=normal
@@ -659,8 +659,8 @@ p1/m1.py:1: error: "int" not callable
 [out]
 main.py:1: error: "int" not callable
 ==
-x.py:1: error: "str" not callable
 main.py:1: error: "int" not callable
+x.py:1: error: "str" not callable
 
 [case testFollowImportsNormalSearchPathUpdate-only_when_nocache]
 # flags: --follow-imports=normal
@@ -678,8 +678,8 @@ import bar
 
 [out]
 ==
-src/bar.py:1: error: "int" not callable
 src/foo.py:2: error: "str" not callable
+src/bar.py:1: error: "int" not callable
 
 [case testFollowImportsNormalSearchPathUpdate2-only_when_cache]
 # flags: --follow-imports=normal
diff --git a/test-data/unit/fine-grained-modules.test b/test-data/unit/fine-grained-modules.test
index dcf28ad35357..f76ced64341b 100644
--- a/test-data/unit/fine-grained-modules.test
+++ b/test-data/unit/fine-grained-modules.test
@@ -38,8 +38,8 @@ def f(x: int) -> None: pass
 ==
 a.py:2: error: Incompatible return value type (got "int", expected "str")
 ==
-b.py:2: error: Too many arguments for "f"
 a.py:2: error: Incompatible return value type (got "int", expected "str")
+b.py:2: error: Too many arguments for "f"
 ==
 
 [case testAddFileFixesError]
diff --git a/test-data/unit/fine-grained.test b/test-data/unit/fine-grained.test
index 27c062531903..49f03a23177e 100644
--- a/test-data/unit/fine-grained.test
+++ b/test-data/unit/fine-grained.test
@@ -1814,9 +1814,9 @@ def f() -> Iterator[None]:
 [out]
 main:2: note: Revealed type is "contextlib.GeneratorContextManager[None]"
 ==
+main:2: note: Revealed type is "contextlib.GeneratorContextManager[None]"
 a.py:3: error: Cannot find implementation or library stub for module named "b"
 a.py:3: note: See https://mypy.readthedocs.io/en/stable/running_mypy.html#missing-imports
-main:2: note: Revealed type is "contextlib.GeneratorContextManager[None]"
 ==
 main:2: note: Revealed type is "contextlib.GeneratorContextManager[None]"
 
@@ -8689,8 +8689,8 @@ main:2: note: Revealed type is "builtins.int"
 ==
 main:2: note: Revealed type is "Literal[1]"
 ==
-mod.py:2: error: Incompatible types in assignment (expression has type "Literal[2]", variable has type "Literal[1]")
 main:2: note: Revealed type is "Literal[1]"
+mod.py:2: error: Incompatible types in assignment (expression has type "Literal[2]", variable has type "Literal[1]")
 
 [case testLiteralFineGrainedFunctionConversion]
 from mod import foo
@@ -9178,10 +9178,10 @@ a.py:1: error: Type signature has too few arguments
 a.py:5: error: Type signature has too few arguments
 a.py:11: error: Type signature has too few arguments
 ==
+c.py:1: error: Type signature has too few arguments
 a.py:1: error: Type signature has too few arguments
 a.py:5: error: Type signature has too few arguments
 a.py:11: error: Type signature has too few arguments
-c.py:1: error: Type signature has too few arguments
 
 [case testErrorReportingNewAnalyzer]
 # flags: --disallow-any-generics
@@ -10072,3 +10072,53 @@ class Base(Protocol):
 [out]
 ==
 main:6: error: Call to abstract method "meth" of "Base" with trivial body via super() is unsafe
+
+[case testPrettyMessageSorting]
+# flags: --pretty
+import a
+
+[file a.py]
+1 + ''
+import b
+
+[file b.py]
+object + 1
+
+[file b.py.2]
+object + 1
+1()
+
+[out]
+b.py:1: error: Unsupported left operand type for + ("Type[object]")
+    object + 1
+    ^
+a.py:1: error: Unsupported operand types for + ("int" and "str")
+    1 + ''
+        ^
+==
+b.py:1: error: Unsupported left operand type for + ("Type[object]")
+    object + 1
+    ^
+b.py:2: error: "int" not callable
+    1()
+    ^
+a.py:1: error: Unsupported operand types for + ("int" and "str")
+    1 + ''
+        ^
+[out version>=3.8]
+b.py:1: error: Unsupported left operand type for + ("Type[object]")
+    object + 1
+    ^~~~~~~~~~
+a.py:1: error: Unsupported operand types for + ("int" and "str")
+    1 + ''
+        ^~
+==
+b.py:1: error: Unsupported left operand type for + ("Type[object]")
+    object + 1
+    ^~~~~~~~~~
+b.py:2: error: "int" not callable
+    1()
+    ^~~
+a.py:1: error: Unsupported operand types for + ("int" and "str")
+    1 + ''
+        ^~