diff --git a/.github/dependabot.yml b/.github/dependabot.yml
index 0141cc25d9c..89be9edc2d3 100644
--- a/.github/dependabot.yml
+++ b/.github/dependabot.yml
@@ -58,7 +58,7 @@ updates:
       - "dependencies"
       - "release-notes:not-required"
     schedule:
-      interval: weekly
+      interval: "monthly"
 
   - package-ecosystem: "npm"
     directories: 
diff --git a/3rdparty/python/requirements.txt b/3rdparty/python/requirements.txt
index 59bf8f144cc..381909dc791 100644
--- a/3rdparty/python/requirements.txt
+++ b/3rdparty/python/requirements.txt
@@ -6,54 +6,45 @@
 
 ansicolors==1.1.8
 chevron==0.14.0
-fasteners==0.16.3
-freezegun==1.2.1
+fasteners==0.20.0
+freezegun==1.5.5
 hdrhistogram==0.10.3
-ijson==3.2.3
-libcst==1.4.0
-packaging==24.2
+ijson==3.4.0.post0
+libcst==1.8.5
+packaging==25.0
 pex==2.66.0
 psutil==5.9.8
 # This should be compatible with pytest.py, although it can be looser so that we don't
 # over-constrain pantsbuild.pants.testutil
 pytest>=7,<9,!=7.1.0,!=7.1.1
-python-lsp-jsonrpc==1.0.0
+python-lsp-jsonrpc==1.1.2
 PyYAML>=6.0,<7.0
-requests[security]>=2.28.1
-setproctitle==1.3.2
-setuptools>=63.1.0,<64.0
+requests[security]==2.32.5
+setproctitle==1.3.7
+setuptools>=63.1.0,<81.0
 toml==0.10.2
-types-freezegun==1.1.6
-types-PyYAML==6.0.3
-types-requests==2.28.1
-types-setuptools==62.6.1
-types-toml==0.10.8
-typing-extensions~=4.12
+types-PyYAML==6.0.12.20250915
+types-requests==2.32.4.20250913
+types-setuptools==80.9.0.20250822
+types-toml==0.10.8.20240310
+typing-extensions==4.15
 mypy-typing-asserts==0.1.1
 node-semver==0.9.0
 
-# In src/python/pants/backend/url_handlers/s3/register.py we advise adding
-# `botocore` to `[GLOBAL].plugins`, but `botocore` is particular about the
-# version of urllib3 used.  To make the s3 handler easier to use, constrain
-# urlib3 here.  Per the voluminous thread at
-# https://github.com/boto/botocore/issues/2926 this can likely be relaxed when
-# Pants itself is on a newer version of Python
-urllib3<2
-
 # These dependencies are only for debugging Pants itself (in VSCode/PyCharm respectively),
 # and should never be imported.
-debugpy==1.8.13
+debugpy==1.8.16
 pydevd-pycharm==251.23536.40
 
 # These dependencies must only be used from the explorer backend, and no code outside that backend
 # may import anything from it, so these libraries are not ending up as requirements of Pants itself.
-fastapi==0.78.0
-starlette==0.19.1
-strawberry-graphql[fastapi]==0.114.0
-uvicorn[standard]==0.17.6
+fastapi==0.120.0
+starlette==0.48.0
+strawberry-graphql[fastapi]==0.284.1
+uvicorn[standard]==0.38.0
 
 beautifulsoup4==4.11.1 # Util for webcrawling for pulling in tool versions
-python-gnupg==0.4.9 # For validating signatures
+python-gnupg==0.5.5 # For validating signatures
 
 # Only used for release management
-PyGithub==2.4.0
+PyGithub==2.8.1
diff --git a/3rdparty/python/user_reqs.lock b/3rdparty/python/user_reqs.lock
index 7cb8f3a67b4..4c5b0758cf9 100644
--- a/3rdparty/python/user_reqs.lock
+++ b/3rdparty/python/user_reqs.lock
@@ -13,100 +13,81 @@
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             }
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-          "project_name": "ansicolors",
+          "project_name": "annotated-doc",
           "requires_dists": [],
-          "requires_python": null,
-          "version": "1.1.8"
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-            "uvloop>=0.17; (python_version < \"3.12\" and platform_python_implementation == \"CPython\" and platform_system != \"Windows\") and extra == \"test\""
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-          "project_name": "backports-cached-property",
+          "project_name": "anyio",
           "requires_dists": [
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+            "exceptiongroup>=1.0.2; python_version < \"3.11\"",
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-              "hash": "cb11ff66657befba94d828e3b622d5fb76f22fbda1376f355f3e6e51e97d9450",
-              "url": "https://files.pythonhosted.org/packages/e8/6e/3904af0715e03fc5b2636cb8cf8b0eabc45b1f2cf6e4cf8453ddb6d23042/watchgod-0.8.2.tar.gz"
+              "hash": "a173cb5c16c4f40ab19cecf48a534c409f7ea983ab8fed0741304a1c0a31b3f2",
+              "url": "https://files.pythonhosted.org/packages/c2/c9/8869df9b2a2d6c59d79220a4db37679e74f807c559ffe5265e08b227a210/watchfiles-1.1.1.tar.gz"
+            },
+            {
+              "algorithm": "sha256",
+              "hash": "b2cd9e04277e756a2e2d2543d65d1e2166d6fd4c9b183f8808634fda23f17b14",
+              "url": "https://files.pythonhosted.org/packages/f4/c3/3c9a55f255aa57b91579ae9e98c88704955fa9dac3e5614fb378291155df/watchfiles-1.1.1-cp311-cp311-manylinux_2_17_i686.manylinux2014_i686.whl"
+            },
+            {
+              "algorithm": "sha256",
+              "hash": "421e29339983e1bebc281fab40d812742268ad057db4aee8c4d2bce0af43b741",
+              "url": "https://files.pythonhosted.org/packages/fe/cd/f515660b1f32f65df671ddf6f85bfaca621aee177712874dc30a97397977/watchfiles-1.1.1-cp311-cp311-macosx_11_0_arm64.whl"
             }
           ],
-          "project_name": "watchgod",
+          "project_name": "watchfiles",
           "requires_dists": [
-            "anyio<4,>=3.0.0"
+            "anyio>=3.0.0"
           ],
-          "requires_python": ">=3.7",
-          "version": "0.8.2"
+          "requires_python": ">=3.9",
+          "version": "1.1.1"
         },
         {
           "artifacts": [
@@ -2173,59 +2203,6 @@
           "requires_dists": [],
           "requires_python": ">=3.9",
           "version": "15.0.1"
-        },
-        {
-          "artifacts": [
-            {
-              "algorithm": "sha256",
-              "hash": "7171ae35d2c33d326ac19dd8facb1e82e5fd04ef8c6c0e394d7af55a55051c22",
-              "url": "https://files.pythonhosted.org/packages/1f/f6/a933bd70f98e9cf3e08167fc5cd7aaaca49147e48411c0bd5ae701bb2194/wrapt-1.17.3-py3-none-any.whl"
-            },
-            {
-              "algorithm": "sha256",
-              "hash": "79573c24a46ce11aab457b472efd8d125e5a51da2d1d24387666cd85f54c05b2",
-              "url": "https://files.pythonhosted.org/packages/1e/d7/4ad5327612173b144998232f98a85bb24b60c352afb73bc48e3e0d2bdc4e/wrapt-1.17.3-cp311-cp311-musllinux_1_2_x86_64.whl"
-            },
-            {
-              "algorithm": "sha256",
-              "hash": "0610b46293c59a3adbae3dee552b648b984176f8562ee0dba099a56cfbe4df1f",
-              "url": "https://files.pythonhosted.org/packages/31/25/3e8cc2c46b5329c5957cec959cb76a10718e1a513309c31399a4dad07eb3/wrapt-1.17.3-cp311-cp311-macosx_11_0_arm64.whl"
-            },
-            {
-              "algorithm": "sha256",
-              "hash": "8cccf4f81371f257440c88faed6b74f1053eef90807b77e31ca057b2db74edb1",
-              "url": "https://files.pythonhosted.org/packages/31/57/4930cb8d9d70d59c27ee1332a318c20291749b4fba31f113c2f8ac49a72e/wrapt-1.17.3-cp311-cp311-manylinux2014_aarch64.manylinux_2_17_aarch64.manylinux_2_28_aarch64.whl"
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-              "algorithm": "sha256",
-              "hash": "273a736c4645e63ac582c60a56b0acb529ef07f78e08dc6bfadf6a46b19c0da7",
-              "url": "https://files.pythonhosted.org/packages/52/db/00e2a219213856074a213503fdac0511203dceefff26e1daa15250cc01a0/wrapt-1.17.3-cp311-cp311-macosx_10_9_universal2.whl"
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-              "algorithm": "sha256",
-              "hash": "b32888aad8b6e68f83a8fdccbf3165f5469702a7544472bdf41f582970ed3311",
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-            },
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-              "algorithm": "sha256",
-              "hash": "f66eb08feaa410fe4eebd17f2a2c8e2e46d3476e9f8c783daa8e09e0faa666d0",
-              "url": "https://files.pythonhosted.org/packages/95/8f/aeb76c5b46e273670962298c23e7ddde79916cb74db802131d49a85e4b7d/wrapt-1.17.3.tar.gz"
-            },
-            {
-              "algorithm": "sha256",
-              "hash": "d8a210b158a34164de8bb68b0e7780041a903d7b00c87e906fb69928bf7890d5",
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-            }
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-          "project_name": "wrapt",
-          "requires_dists": [],
-          "requires_python": ">=3.8",
-          "version": "1.17.3"
         }
       ],
       "marker": null,
@@ -2240,41 +2217,39 @@
   "pip_version": "25.3",
   "prefer_older_binary": false,
   "requirements": [
-    "PyGithub==2.4.0",
+    "PyGithub==2.8.1",
     "PyYAML<7.0,>=6.0",
     "ansicolors==1.1.8",
     "beautifulsoup4==4.11.1",
     "chevron==0.14.0",
-    "debugpy==1.8.13",
-    "fastapi==0.78.0",
-    "fasteners==0.16.3",
-    "freezegun==1.2.1",
+    "debugpy==1.8.16",
+    "fastapi==0.120.0",
+    "fasteners==0.20.0",
+    "freezegun==1.5.5",
     "hdrhistogram==0.10.3",
-    "ijson==3.2.3",
-    "libcst==1.4.0",
+    "ijson==3.4.0.post0",
+    "libcst==1.8.5",
     "mypy-typing-asserts==0.1.1",
     "node-semver==0.9.0",
-    "packaging==24.2",
+    "packaging==25.0",
     "pex==2.66.0",
     "psutil==5.9.8",
     "pydevd-pycharm==251.23536.40",
     "pytest!=7.1.0,!=7.1.1,<9,>=7",
-    "python-gnupg==0.4.9",
-    "python-lsp-jsonrpc==1.0.0",
-    "requests[security]>=2.28.1",
-    "setproctitle==1.3.2",
-    "setuptools<64.0,>=63.1.0",
-    "starlette==0.19.1",
-    "strawberry-graphql[fastapi]==0.114.0",
+    "python-gnupg==0.5.5",
+    "python-lsp-jsonrpc==1.1.2",
+    "requests[security]==2.32.5",
+    "setproctitle==1.3.7",
+    "setuptools<81.0,>=63.1.0",
+    "starlette==0.48.0",
+    "strawberry-graphql[fastapi]==0.284.1",
     "toml==0.10.2",
-    "types-PyYAML==6.0.3",
-    "types-freezegun==1.1.6",
-    "types-requests==2.28.1",
-    "types-setuptools==62.6.1",
-    "types-toml==0.10.8",
-    "typing-extensions~=4.12",
-    "urllib3<2",
-    "uvicorn[standard]==0.17.6"
+    "types-PyYAML==6.0.12.20250915",
+    "types-requests==2.32.4.20250913",
+    "types-setuptools==80.9.0.20250822",
+    "types-toml==0.10.8.20240310",
+    "typing-extensions==4.15",
+    "uvicorn[standard]==0.38.0"
   ],
   "requires_python": [
     "CPython==3.11.*"
diff --git a/3rdparty/python/user_reqs.lock.metadata b/3rdparty/python/user_reqs.lock.metadata
index ba98e756d62..11306f2cf05 100644
--- a/3rdparty/python/user_reqs.lock.metadata
+++ b/3rdparty/python/user_reqs.lock.metadata
@@ -4,41 +4,39 @@
     "CPython==3.11.*"
   ],
   "generated_with_requirements": [
-    "PyGithub==2.4.0",
+    "PyGithub==2.8.1",
     "PyYAML<7.0,>=6.0",
     "ansicolors==1.1.8",
     "beautifulsoup4==4.11.1",
     "chevron==0.14.0",
-    "debugpy==1.8.13",
-    "fastapi==0.78.0",
-    "fasteners==0.16.3",
-    "freezegun==1.2.1",
+    "debugpy==1.8.16",
+    "fastapi==0.120.0",
+    "fasteners==0.20.0",
+    "freezegun==1.5.5",
     "hdrhistogram==0.10.3",
-    "ijson==3.2.3",
-    "libcst==1.4.0",
+    "ijson==3.4.0.post0",
+    "libcst==1.8.5",
     "mypy-typing-asserts==0.1.1",
     "node-semver==0.9.0",
-    "packaging==24.2",
+    "packaging==25.0",
     "pex==2.66.0",
     "psutil==5.9.8",
     "pydevd-pycharm==251.23536.40",
     "pytest!=7.1.0,!=7.1.1,<9,>=7",
-    "python-gnupg==0.4.9",
-    "python-lsp-jsonrpc==1.0.0",
-    "requests[security]>=2.28.1",
-    "setproctitle==1.3.2",
-    "setuptools<64.0,>=63.1.0",
-    "starlette==0.19.1",
-    "strawberry-graphql[fastapi]==0.114.0",
+    "python-gnupg==0.5.5",
+    "python-lsp-jsonrpc==1.1.2",
+    "requests[security]==2.32.5",
+    "setproctitle==1.3.7",
+    "setuptools<81.0,>=63.1.0",
+    "starlette==0.48.0",
+    "strawberry-graphql[fastapi]==0.284.1",
     "toml==0.10.2",
-    "types-PyYAML==6.0.3",
-    "types-freezegun==1.1.6",
-    "types-requests==2.28.1",
-    "types-setuptools==62.6.1",
-    "types-toml==0.10.8",
-    "typing-extensions~=4.12",
-    "urllib3<2",
-    "uvicorn[standard]==0.17.6"
+    "types-PyYAML==6.0.12.20250915",
+    "types-requests==2.32.4.20250913",
+    "types-setuptools==80.9.0.20250822",
+    "types-toml==0.10.8.20240310",
+    "typing-extensions==4.15",
+    "uvicorn[standard]==0.38.0"
   ],
   "manylinux": "manylinux2014",
   "requirement_constraints": [],
diff --git a/pants-plugins/pants_explorer/server/graphql/query/targets.py b/pants-plugins/pants_explorer/server/graphql/query/targets.py
index e932d831b91..b8f39faf672 100644
--- a/pants-plugins/pants_explorer/server/graphql/query/targets.py
+++ b/pants-plugins/pants_explorer/server/graphql/query/targets.py
@@ -63,7 +63,7 @@ class Target:
     target_type: str = strawberry.field(
         description="The target type, such as `python_sources` or `pex_binary` etc."
     )
-    fields: JSONScalar = strawberry.field(  # type: ignore[valid-type]
+    fields: JSONScalar = strawberry.field(
         description=softwrap(
             """
             The targets field values. This has the same structure as the JSON output from the `peek`
@@ -78,7 +78,7 @@ def from_data(cls, data: TargetData) -> Target:
         address = json.pop("address")
         target_type = json.pop("target_type")
         fields = json
-        return cls(address=address, target_type=target_type, fields=fields)  # type: ignore[call-arg]
+        return cls(address=address, target_type=target_type, fields=fields)
 
 
 @strawberry.input(
diff --git a/pants-plugins/pants_explorer/server/uvicorn.py b/pants-plugins/pants_explorer/server/uvicorn.py
index 22d2c5a8860..4f8d460f103 100644
--- a/pants-plugins/pants_explorer/server/uvicorn.py
+++ b/pants-plugins/pants_explorer/server/uvicorn.py
@@ -10,7 +10,7 @@
 
 from fastapi import FastAPI
 from pants_explorer.server.browser import BrowserRequest
-from uvicorn import Config, Server  # type: ignore
+from uvicorn import Config, Server
 
 from pants.base.exiter import ExitCode
 from pants.engine.environment import EnvironmentName
@@ -44,7 +44,7 @@ def from_request(cls, request: UvicornServerRequest) -> UvicornServer:
                 app,
                 host=request.address,
                 port=request.port,
-                timeout_notify=0.25,
+                timeout_notify=1,
                 log_config=None,
             ),
             request_state=request.request_state,
diff --git a/src/python/pants/backend/helm/util_rules/chart_metadata.py b/src/python/pants/backend/helm/util_rules/chart_metadata.py
index a01caed09f9..53042054d87 100644
--- a/src/python/pants/backend/helm/util_rules/chart_metadata.py
+++ b/src/python/pants/backend/helm/util_rules/chart_metadata.py
@@ -6,7 +6,7 @@
 import dataclasses
 from dataclasses import dataclass
 from enum import Enum
-from typing import Any, cast
+from typing import Any
 
 import yaml
 
@@ -208,7 +208,7 @@ def to_json_dict(self) -> dict[str, Any]:
         return d
 
     def to_yaml(self) -> str:
-        return cast("str", yaml.dump(self.to_json_dict()))
+        return yaml.dump(self.to_json_dict())
 
 
 HELM_CHART_METADATA_FILENAMES = ["Chart.yaml", "Chart.yml"]