diff --git a/.github/workflows/update-reproducibles.yml b/.github/workflows/update-reproducibles.yml
index f98395c93f..9101f28c7c 100644
--- a/.github/workflows/update-reproducibles.yml
+++ b/.github/workflows/update-reproducibles.yml
@@ -25,7 +25,7 @@ jobs:
             python: 3.8
             target: update-reproducible-mac-reqs
           - os: windows-latest
-            python: 3.8
+            python: 3.11
             target: update-reproducible-win-reqs
       max-parallel: 1
     runs-on: ${{ matrix.os }}
diff --git a/appveyor-windows-binary.yml b/appveyor-windows-binary.yml
index 6432e88513..54e1385928 100644
--- a/appveyor-windows-binary.yml
+++ b/appveyor-windows-binary.yml
@@ -25,10 +25,10 @@ environment:
   TMPDIR: "%TEMP%"
   TMP: "%TEMP%"
 
-  # MSI Installers only use Py3.8. It is sufficient to test with this version here.
-  PYTHON_HOME: "C:\\Python38-x64"
-  PYTHON_SCRIPTS: "C:\\Python38-x64\\Scripts"
-  PYTHON_EXE: "C:\\Python38-x64\\python.exe"
+  # MSI Installers only use Py3.11. It is sufficient to test with this version here.
+  PYTHON_HOME: "C:\\Python311-x64"
+  PYTHON_SCRIPTS: "C:\\Python311-x64\\Scripts"
+  PYTHON_EXE: "C:\\Python311-x64\\python.exe"
   PYTHON_ARCH: "64"
   HOME: 'C:\Users\appveyor'
   HOMEDRIVE: "C:"
@@ -67,7 +67,7 @@ install:
 
   # Make sure the temp directory exists for Python to use.
   - ps: "mkdir -Force C:\\tmp"
-  - 'set PATH=%PYTHON_HOME%;C:\Ruby32-x64\bin;%PATH%;C:\Python37-x64;C:\Python39-x64;C:\Python310-x64;C:\Python311-x64'
+  - 'set PATH=%PYTHON_HOME%;C:\Ruby32-x64\bin;%PATH%;C:\Python37-x64;C:\Python39-x64;C:\Python310-x64;C:\Python38-x64'
   - "echo %PYTHON_HOME%"
   - "echo %PATH%"
   - "python --version"
diff --git a/requirements/reproducible-win.txt b/requirements/reproducible-win.txt
index 44e3d09fc3..3e921c2d76 100644
--- a/requirements/reproducible-win.txt
+++ b/requirements/reproducible-win.txt
@@ -1,5 +1,5 @@
 #
-# This file is autogenerated by pip-compile with Python 3.8
+# This file is autogenerated by pip-compile with Python 3.11
 # by the following command:
 #
 #    pip-compile --allow-unsafe --generate-hashes --output-file='requirements\reproducible-win.txt'
@@ -30,24 +30,6 @@ aws-sam-translator==1.79.0 \
     # via
     #   aws-sam-cli (setup.py)
     #   cfn-lint
-backports-zoneinfo==0.2.1 \
-    --hash=sha256:17746bd546106fa389c51dbea67c8b7c8f0d14b5526a579ca6ccf5ed72c526cf \
-    --hash=sha256:1b13e654a55cd45672cb54ed12148cd33628f672548f373963b0bff67b217328 \
-    --hash=sha256:1c5742112073a563c81f786e77514969acb58649bcdf6cdf0b4ed31a348d4546 \
-    --hash=sha256:4a0f800587060bf8880f954dbef70de6c11bbe59c673c3d818921f042f9954a6 \
-    --hash=sha256:5c144945a7752ca544b4b78c8c41544cdfaf9786f25fe5ffb10e838e19a27570 \
-    --hash=sha256:7b0a64cda4145548fed9efc10322770f929b944ce5cee6c0dfe0c87bf4c0c8c9 \
-    --hash=sha256:8439c030a11780786a2002261569bdf362264f605dfa4d65090b64b05c9f79a7 \
-    --hash=sha256:8961c0f32cd0336fb8e8ead11a1f8cd99ec07145ec2931122faaac1c8f7fd987 \
-    --hash=sha256:89a48c0d158a3cc3f654da4c2de1ceba85263fafb861b98b59040a5086259722 \
-    --hash=sha256:a76b38c52400b762e48131494ba26be363491ac4f9a04c1b7e92483d169f6582 \
-    --hash=sha256:da6013fd84a690242c310d77ddb8441a559e9cb3d3d59ebac9aca1a57b2e18bc \
-    --hash=sha256:e55b384612d93be96506932a786bbcde5a2db7a9e6a4bb4bffe8b733f5b9036b \
-    --hash=sha256:e81b76cace8eda1fca50e345242ba977f9be6ae3945af8d46326d776b4cf78d1 \
-    --hash=sha256:e8236383a20872c0cdf5a62b554b27538db7fa1bbec52429d8d106effbaeca08 \
-    --hash=sha256:f04e857b59d9d1ccc39ce2da1021d196e47234873820cbeaad210724b1ee28ac \
-    --hash=sha256:fadbfe37f74051d024037f223b8e001611eac868b5c5b06144ef4d8b799862f2
-    # via tzlocal
 binaryornot==0.4.4 \
     --hash=sha256:359501dfc9d40632edc9fac890e19542db1a287bbcfa58175b66658392018061 \
     --hash=sha256:b8b71173c917bddcd2c16070412e369c3ed7f0528926f70cac18a6c97fd563e4
@@ -296,16 +278,6 @@ idna==3.4 \
     --hash=sha256:814f528e8dead7d329833b91c5faa87d60bf71824cd12a7530b5526063d02cb4 \
     --hash=sha256:90b77e79eaa3eba6de819a0c442c0b4ceefc341a7a2ab77d7562bf49f425c5c2
     # via requests
-importlib-metadata==6.8.0 \
-    --hash=sha256:3ebb78df84a805d7698245025b975d9d67053cd94c79245ba4b3eb694abe68bb \
-    --hash=sha256:dbace7892d8c0c4ac1ad096662232f831d4e64f4c4545bd53016a3e9d4654743
-    # via flask
-importlib-resources==6.1.0 \
-    --hash=sha256:9d48dcccc213325e810fd723e7fbb45ccb39f6cf5c31f00cf2b965f5f10f3cb9 \
-    --hash=sha256:aa50258bbfa56d4e33fbd8aa3ef48ded10d1735f11532b8df95388cc6bdb7e83
-    # via
-    #   jsonschema
-    #   jsonschema-specifications
 itsdangerous==2.1.2 \
     --hash=sha256:2c2349112351b88699d8d4b6b075022c0808887cb7ad10069318a8b0bc88db44 \
     --hash=sha256:5dbbc68b317e5e42f327f9021763545dc3fc3bfe22e6deb96aaf1fc38874156a
@@ -490,10 +462,6 @@ pbr==5.11.1 \
     # via
     #   jschema-to-python
     #   sarif-om
-pkgutil-resolve-name==1.3.10 \
-    --hash=sha256:357d6c9e6a755653cfd78893817c0853af365dd51ec97f3d358a819373bbd174 \
-    --hash=sha256:ca27cc078d25c5ad71a9de0a7a330146c4e014c2462d9af19c6b828280649c5e
-    # via jsonschema
 pycparser==2.21 \
     --hash=sha256:8ee45429555515e1f6b185e78100aea234072576aa43ab53aefcae078162fca9 \
     --hash=sha256:e644fdec12f7872f86c58ff790da456218b10f863970249516d60a5eaca77206
@@ -994,11 +962,9 @@ typing-extensions==4.8.0 \
     --hash=sha256:8f92fc8806f9a6b641eaa5318da32b44d401efaac0f6678c9bc448ba3605faa0 \
     --hash=sha256:df8e4339e9cb77357558cbdbceca33c303714cf861d1eef15e1070055ae8b7ef
     # via
-    #   annotated-types
     #   aws-sam-cli (setup.py)
     #   aws-sam-translator
     #   boto3-stubs
-    #   botocore-stubs
     #   mypy-boto3-apigateway
     #   mypy-boto3-cloudformation
     #   mypy-boto3-ecr
@@ -1015,7 +981,6 @@ typing-extensions==4.8.0 \
     #   mypy-boto3-xray
     #   pydantic
     #   pydantic-core
-    #   rich
 tzdata==2023.3 \
     --hash=sha256:11ef1e08e54acb0d4f95bdb1be05da659673de4acbd21bf9c69e94cc5e907a3a \
     --hash=sha256:7e65763eef3120314099b6939b5546db7adce1e7d6f2e179e3df563c70511eda
@@ -1074,12 +1039,6 @@ wheel==0.41.2 \
     --hash=sha256:0c5ac5ff2afb79ac23ab82bab027a0be7b5dbcf2e54dc50efe4bf507de1f7985 \
     --hash=sha256:75909db2664838d015e3d9139004ee16711748a52c8f336b52882266540215d8
     # via aws-lambda-builders
-zipp==3.17.0 \
-    --hash=sha256:0e923e726174922dce09c53c59ad483ff7bbb8e572e00c7f7c46b88556409f31 \
-    --hash=sha256:84e64a1c28cf7e91ed2078bb8cc8c259cb19b76942096c8d7b84947690cabaf0
-    # via
-    #   importlib-metadata
-    #   importlib-resources
 
 # The following packages are considered to be unsafe in a requirements file:
 setuptools==68.2.2 \