diff --git a/.github/workflows/test-integrations-cloud.yml b/.github/workflows/test-integrations-cloud.yml
index 8688a1d48e..62e70d759d 100644
--- a/.github/workflows/test-integrations-cloud.yml
+++ b/.github/workflows/test-integrations-cloud.yml
@@ -22,85 +22,6 @@ env:
   CACHED_BUILD_PATHS: |
     ${{ github.workspace }}/dist-serverless
 jobs:
-  test-cloud-latest:
-    name: Cloud (latest)
-    timeout-minutes: 30
-    runs-on: ${{ matrix.os }}
-    strategy:
-      fail-fast: false
-      matrix:
-        python-version: ["3.8","3.12","3.13"]
-        # python3.6 reached EOL and is no longer being supported on
-        # new versions of hosted runners on Github Actions
-        # ubuntu-20.04 is the last version that supported python3.6
-        # see https://github.com/actions/setup-python/issues/544#issuecomment-1332535877
-        os: [ubuntu-22.04]
-    services:
-      docker:
-        image: docker:dind  # Required for Docker network management
-        options: --privileged  # Required for Docker-in-Docker operations
-    # Use Docker container only for Python 3.6
-    container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
-    steps:
-      - uses: actions/checkout@v5.0.0
-      - uses: actions/setup-python@v5
-        if: ${{ matrix.python-version != '3.6' }}
-        with:
-          python-version: ${{ matrix.python-version }}
-          allow-prereleases: true
-      - name: Setup Test Env
-        run: |
-          pip install "coverage[toml]" tox
-      - name: Erase coverage
-        run: |
-          coverage erase
-      - name: Test aws_lambda latest
-        run: |
-          set -x # print commands that are executed
-          ./scripts/runtox.sh "py${{ matrix.python-version }}-aws_lambda-latest"
-      - name: Test boto3 latest
-        run: |
-          set -x # print commands that are executed
-          ./scripts/runtox.sh "py${{ matrix.python-version }}-boto3-latest"
-      - name: Test chalice latest
-        run: |
-          set -x # print commands that are executed
-          ./scripts/runtox.sh "py${{ matrix.python-version }}-chalice-latest"
-      - name: Test cloud_resource_context latest
-        run: |
-          set -x # print commands that are executed
-          ./scripts/runtox.sh "py${{ matrix.python-version }}-cloud_resource_context-latest"
-      - name: Test gcp latest
-        run: |
-          set -x # print commands that are executed
-          ./scripts/runtox.sh "py${{ matrix.python-version }}-gcp-latest"
-      - name: Generate coverage XML (Python 3.6)
-        if: ${{ !cancelled() && matrix.python-version == '3.6' }}
-        run: |
-          export COVERAGE_RCFILE=.coveragerc36
-          coverage combine .coverage-sentry-*
-          coverage xml --ignore-errors
-      - name: Generate coverage XML
-        if: ${{ !cancelled() && matrix.python-version != '3.6' }}
-        run: |
-          coverage combine .coverage-sentry-*
-          coverage xml
-      - name: Upload coverage to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.0
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
-          verbose: true
   test-cloud-pinned:
     name: Cloud (pinned)
     timeout-minutes: 30
diff --git a/scripts/populate_tox/config.py b/scripts/populate_tox/config.py
index 5aba82b11b..b05c4297f1 100644
--- a/scripts/populate_tox/config.py
+++ b/scripts/populate_tox/config.py
@@ -66,6 +66,12 @@
             "py3.7": ["importlib-metadata<5.0"],
         },
     },
+    "chalice": {
+        "package": "chalice",
+        "deps": {
+            "*": ["pytest-chalice"],
+        },
+    },
     "clickhouse_driver": {
         "package": "clickhouse-driver",
     },
diff --git a/scripts/populate_tox/populate_tox.py b/scripts/populate_tox/populate_tox.py
index b8cc988fda..9aed9fa718 100644
--- a/scripts/populate_tox/populate_tox.py
+++ b/scripts/populate_tox/populate_tox.py
@@ -67,7 +67,6 @@
     "potel",
     # Integrations that can be migrated -- we should eventually remove all
     # of these from the IGNORE list
-    "chalice",
     "gcp",
     "httpx",
     "pure_eval",
diff --git a/scripts/populate_tox/tox.jinja b/scripts/populate_tox/tox.jinja
index 7f23d1fbc7..c243b5752e 100755
--- a/scripts/populate_tox/tox.jinja
+++ b/scripts/populate_tox/tox.jinja
@@ -42,10 +42,6 @@ envlist =
     # AWS Lambda
     {py3.8,py3.9,py3.11,py3.13}-aws_lambda
 
-    # Chalice
-    {py3.6,py3.9}-chalice-v{1.16}
-    {py3.8,py3.12,py3.13}-chalice-latest
-
     # Cloud Resource Context
     {py3.6,py3.12,py3.13}-cloud_resource_context
 
@@ -158,11 +154,6 @@ deps =
     aws_lambda: requests
     aws_lambda: uvicorn
 
-    # Chalice
-    chalice: pytest-chalice==0.0.5
-    chalice-v1.16: chalice~=1.16.0
-    chalice-latest: chalice
-
     # HTTPX
     httpx-v0.16: pytest-httpx==0.10.0
     httpx-v0.18: pytest-httpx==0.12.0
diff --git a/tests/integrations/chalice/test_chalice.py b/tests/integrations/chalice/test_chalice.py
index fbd4be4e59..ec8106eb5f 100644
--- a/tests/integrations/chalice/test_chalice.py
+++ b/tests/integrations/chalice/test_chalice.py
@@ -110,7 +110,7 @@ def every_hour(event):
 
 
 @pytest.mark.skipif(
-    parse_version(CHALICE_VERSION) >= (1, 28),
+    parse_version(CHALICE_VERSION) >= (1, 26, 0),
     reason="different behavior based on chalice version",
 )
 def test_bad_request_old(client: RequestHandler) -> None:
@@ -124,7 +124,7 @@ def test_bad_request_old(client: RequestHandler) -> None:
 
 
 @pytest.mark.skipif(
-    parse_version(CHALICE_VERSION) < (1, 28),
+    parse_version(CHALICE_VERSION) < (1, 26, 0),
     reason="different behavior based on chalice version",
 )
 def test_bad_request(client: RequestHandler) -> None:
diff --git a/tox.ini b/tox.ini
index 948887f1dd..335007664a 100644
--- a/tox.ini
+++ b/tox.ini
@@ -10,7 +10,7 @@
 # The file (and all resulting CI YAMLs) then need to be regenerated via
 # "scripts/generate-test-files.sh".
 #
-# Last generated: 2025-09-05T07:14:50.663886+00:00
+# Last generated: 2025-09-05T07:52:27.350774+00:00
 
 [tox]
 requires =
@@ -42,10 +42,6 @@ envlist =
     # AWS Lambda
     {py3.8,py3.9,py3.11,py3.13}-aws_lambda
 
-    # Chalice
-    {py3.6,py3.9}-chalice-v{1.16}
-    {py3.8,py3.12,py3.13}-chalice-latest
-
     # Cloud Resource Context
     {py3.6,py3.12,py3.13}-cloud_resource_context
 
@@ -152,6 +148,11 @@ envlist =
     {py3.7,py3.11,py3.12}-boto3-v1.28.85
     {py3.9,py3.12,py3.13}-boto3-v1.40.24
 
+    {py3.6,py3.7,py3.8}-chalice-v1.16.0
+    {py3.6,py3.7,py3.8}-chalice-v1.21.9
+    {py3.6,py3.8,py3.9}-chalice-v1.26.6
+    {py3.9,py3.12,py3.13}-chalice-v1.32.0
+
 
     # ~~~ DBs ~~~
     {py3.7,py3.8,py3.9}-asyncpg-v0.23.0
@@ -372,11 +373,6 @@ deps =
     aws_lambda: requests
     aws_lambda: uvicorn
 
-    # Chalice
-    chalice: pytest-chalice==0.0.5
-    chalice-v1.16: chalice~=1.16.0
-    chalice-latest: chalice
-
     # HTTPX
     httpx-v0.16: pytest-httpx==0.10.0
     httpx-v0.18: pytest-httpx==0.12.0
@@ -541,6 +537,12 @@ deps =
     boto3-v1.40.24: boto3==1.40.24
     {py3.7,py3.8}-boto3: urllib3<2.0.0
 
+    chalice-v1.16.0: chalice==1.16.0
+    chalice-v1.21.9: chalice==1.21.9
+    chalice-v1.26.6: chalice==1.26.6
+    chalice-v1.32.0: chalice==1.32.0
+    chalice: pytest-chalice
+
 
     # ~~~ DBs ~~~
     asyncpg-v0.23.0: asyncpg==0.23.0