diff --git a/changelog.d/6146.bugfix b/changelog.d/6146.bugfix
new file mode 100644
index 000000000..1dad80183
--- /dev/null
+++ b/changelog.d/6146.bugfix
@@ -0,0 +1,1 @@
+Fix exceptions when storing large retry intervals for down remote servers.
diff --git a/synapse/storage/schema/delta/56/destinations_retry_interval_type.sql.postgres b/synapse/storage/schema/delta/56/destinations_retry_interval_type.sql.postgres
new file mode 100644
index 000000000..b9bbb18a9
--- /dev/null
+++ b/synapse/storage/schema/delta/56/destinations_retry_interval_type.sql.postgres
@@ -0,0 +1,18 @@
+/* Copyright 2019 The Matrix.org Foundation C.I.C
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *    http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+-- We want to store large retry intervals so we upgrade the column from INT
+-- to BIGINT. We don't need to do this on SQLite.
+ALTER TABLE destinations ALTER retry_interval SET DATA TYPE BIGINT;
diff --git a/synapse/util/retryutils.py b/synapse/util/retryutils.py
index a5f2fbef5..af6958719 100644
--- a/synapse/util/retryutils.py
+++ b/synapse/util/retryutils.py
@@ -29,7 +29,7 @@ MIN_RETRY_INTERVAL = 10 * 60 * 1000
 RETRY_MULTIPLIER = 5
 
 # a cap on the backoff. (Essentially none)
-MAX_RETRY_INTERVAL = 2 ** 63
+MAX_RETRY_INTERVAL = 2 ** 62
 
 
 class NotRetryingDestination(Exception):

Failed to store destination_retry_timings:  integer out of range
it is trying to store the retry interval in an integer field, and 2^31 ms is only 25 days, and it's supposed to go a lot higher than that
diff --git a/tests/storage/test_transactions.py b/tests/storage/test_transactions.py
index a771d5af2..8e817e2c7 100644
--- a/tests/storage/test_transactions.py
+++ b/tests/storage/test_transactions.py
@@ -13,6 +13,8 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+from synapse.util.retryutils import MAX_RETRY_INTERVAL
+
 from tests.unittest import HomeserverTestCase
 
 
@@ -45,3 +47,12 @@ class TransactionStoreTestCase(HomeserverTestCase):
         """
         d = self.store.set_destination_retry_timings("example.com", 1000, 50, 100)
         self.get_success(d)
+
+    def test_large_destination_retry(self):
+        d = self.store.set_destination_retry_timings(
+            "example.com", MAX_RETRY_INTERVAL, MAX_RETRY_INTERVAL, MAX_RETRY_INTERVAL
+        )
+        self.get_success(d)
+
+        d = self.store.get_destination_retry_timings("example.com")
+        self.get_success(d)

pip install -e .[all]
parse_log_pytest
pytest
pytest coverage coverage-enable-subprocess
apt-get update apt-get install -y build-essential python3-dev libffi-dev libssl-dev
3.6
pytest --no-header -rA --tb=line --color=no -p no:cacheprovider -W ignore::DeprecationWarning
acme==0.40.1
aiocontextvars==0.2.2
attrs @ file:///opt/conda/conda-bld/attrs_1642510447205/work
Automat==22.10.0
bcrypt==4.0.1
bleach==4.1.0
boltons==23.1.1
canonicaljson==1.5.0
certifi==2021.5.30
cffi==1.15.1
charset-normalizer==2.0.12
constantly==15.1.0
contextvars==2.4
coverage==6.2
coverage-enable-subprocess==1.0
cryptography==40.0.2
daemonize==2.5.0
defusedxml==0.7.1
elementpath==2.4.0
eliot==1.14.0
frozendict==2.4.6
hyperlink==21.0.0
idna==3.10
immutables==0.19
importlib-metadata @ file:///tmp/build/80754af9/importlib-metadata_1631916693255/work
importlib-resources==5.4.0
incremental==22.10.0
iniconfig @ file:///home/linux1/recipes/ci/iniconfig_1610983019677/work
jaeger-client==4.6.1
Jinja2==3.0.3
josepy==1.13.0
jsonschema==3.2.0
ldap3==2.9.1
lxml==5.3.1
MarkupSafe==2.0.1
-e git+https://github.com/matrix-org/synapse.git@dfe70096392b005b81aea551e629ec9aa45ca60e#egg=matrix_synapse
matrix-synapse-ldap3==0.1.5
mock==5.2.0
more-itertools @ file:///tmp/build/80754af9/more-itertools_1637733554872/work
msgpack==1.0.5
netaddr==0.10.1
opentracing==2.4.0
packaging @ file:///tmp/build/80754af9/packaging_1637314298585/work
parameterized==0.8.1
pem==21.2.0
phonenumbers==9.0.2
Pillow==8.4.0
pluggy @ file:///tmp/build/80754af9/pluggy_1615976315926/work
prometheus-client==0.7.1
psutil==7.0.0
psycopg2==2.7.7
py @ file:///opt/conda/conda-bld/py_1644396412707/work
pyasn1==0.5.1
pyasn1-modules==0.3.0
pycparser==2.21
PyJWT==2.4.0
pymacaroons==0.13.0
PyNaCl==1.5.0
pyOpenSSL==23.2.0
pyparsing @ file:///tmp/build/80754af9/pyparsing_1635766073266/work
pyRFC3339==2.0.1
pyrsistent==0.18.0
pysaml2==7.3.1
pytest==6.2.4
python-dateutil==2.9.0.post0
pytz==2025.2
PyYAML==6.0.1
requests==2.27.1
requests-toolbelt==1.0.0
sentry-sdk==2.24.1
service-identity==21.1.0
signedjson==1.1.4
simplejson==3.20.1
six==1.17.0
sortedcontainers==2.4.0
threadloop==1.0.2
thrift==0.21.0
toml @ file:///tmp/build/80754af9/toml_1616166611790/work
tornado==6.1
treq==22.2.0
Twisted==22.4.0
txacme==0.9.3
TxSNI==0.2.0
typing_extensions @ file:///opt/conda/conda-bld/typing_extensions_1647553014482/work
unpaddedbase64==2.1.0
urllib3==1.26.20
webencodings==0.5.1
xmlschema==1.9.2
zipp @ file:///tmp/build/80754af9/zipp_1633618647012/work
zope.interface==5.5.2

name: synapse
channels:
  - defaults
  - https://repo.anaconda.com/pkgs/main
  - https://repo.anaconda.com/pkgs/r
  - conda-forge
dependencies:
  - _libgcc_mutex=0.1=main
  - _openmp_mutex=5.1=1_gnu
  - attrs=21.4.0=pyhd3eb1b0_0
  - ca-certificates=2025.2.25=h06a4308_0
  - certifi=2021.5.30=py36h06a4308_0
  - importlib-metadata=4.8.1=py36h06a4308_0
  - importlib_metadata=4.8.1=hd3eb1b0_0
  - iniconfig=1.1.1=pyhd3eb1b0_0
  - ld_impl_linux-64=2.40=h12ee557_0
  - libffi=3.3=he6710b0_2
  - libgcc-ng=11.2.0=h1234567_1
  - libgomp=11.2.0=h1234567_1
  - libstdcxx-ng=11.2.0=h1234567_1
  - more-itertools=8.12.0=pyhd3eb1b0_0
  - ncurses=6.4=h6a678d5_0
  - openssl=1.1.1w=h7f8727e_0
  - packaging=21.3=pyhd3eb1b0_0
  - pip=21.2.2=py36h06a4308_0
  - pluggy=0.13.1=py36h06a4308_0
  - py=1.11.0=pyhd3eb1b0_0
  - pyparsing=3.0.4=pyhd3eb1b0_0
  - pytest=6.2.4=py36h06a4308_2
  - python=3.6.13=h12debd9_1
  - readline=8.2=h5eee18b_0
  - setuptools=58.0.4=py36h06a4308_0
  - sqlite=3.45.3=h5eee18b_0
  - tk=8.6.14=h39e8969_0
  - toml=0.10.2=pyhd3eb1b0_0
  - typing_extensions=4.1.1=pyh06a4308_0
  - wheel=0.37.1=pyhd3eb1b0_0
  - xz=5.6.4=h5eee18b_1
  - zipp=3.6.0=pyhd3eb1b0_0
  - zlib=1.2.13=h5eee18b_1
  - pip:
      - acme==0.40.1
      - aiocontextvars==0.2.2
      - automat==22.10.0
      - bcrypt==4.0.1
      - bleach==4.1.0
      - boltons==23.1.1
      - canonicaljson==1.5.0
      - cffi==1.15.1
      - charset-normalizer==2.0.12
      - constantly==15.1.0
      - contextvars==2.4
      - coverage==6.2
      - coverage-enable-subprocess==1.0
      - cryptography==40.0.2
      - daemonize==2.5.0
      - defusedxml==0.7.1
      - elementpath==2.4.0
      - eliot==1.14.0
      - frozendict==2.4.6
      - hyperlink==21.0.0
      - idna==3.10
      - immutables==0.19
      - importlib-resources==5.4.0
      - incremental==22.10.0
      - jaeger-client==4.6.1
      - jinja2==3.0.3
      - josepy==1.13.0
      - jsonschema==3.2.0
      - ldap3==2.9.1
      - lxml==5.3.1
      - markupsafe==2.0.1
      - matrix-synapse-ldap3==0.1.5
      - mock==5.2.0
      - msgpack==1.0.5
      - netaddr==0.10.1
      - opentracing==2.4.0
      - parameterized==0.8.1
      - pem==21.2.0
      - phonenumbers==9.0.2
      - pillow==8.4.0
      - prometheus-client==0.7.1
      - psutil==7.0.0
      - psycopg2==2.7.7
      - pyasn1==0.5.1
      - pyasn1-modules==0.3.0
      - pycparser==2.21
      - pyjwt==2.4.0
      - pymacaroons==0.13.0
      - pynacl==1.5.0
      - pyopenssl==23.2.0
      - pyrfc3339==2.0.1
      - pyrsistent==0.18.0
      - pysaml2==7.3.1
      - python-dateutil==2.9.0.post0
      - pytz==2025.2
      - pyyaml==6.0.1
      - requests==2.27.1
      - requests-toolbelt==1.0.0
      - sentry-sdk==2.24.1
      - service-identity==21.1.0
      - signedjson==1.1.4
      - simplejson==3.20.1
      - six==1.17.0
      - sortedcontainers==2.4.0
      - threadloop==1.0.2
      - thrift==0.21.0
      - tornado==6.1
      - treq==22.2.0
      - twisted==22.4.0
      - txacme==0.9.3
      - txsni==0.2.0
      - unpaddedbase64==2.1.0
      - urllib3==1.26.20
      - webencodings==0.5.1
      - xmlschema==1.9.2
      - zope-interface==5.5.2
prefix: /opt/conda/envs/synapse

tests/storage/test_transactions.py::TransactionStoreTestCase::test_large_destination_retry
tests/storage/test_transactions.py::TransactionStoreTestCase::test_get_set_transactions tests/storage/test_transactions.py::TransactionStoreTestCase::test_initial_set_transactions
synapse/util/retryutils.py changelog.d/6146.bugfix synapse/storage/schema/delta/56/destinations_retry_interval_type.sql.postgres
synapse/util/retryutils.py changelog.d/6146.bugfix synapse/storage/schema/delta/56/destinations_retry_interval_type.sql.postgres