diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 4cd3cfc3c93..89de4f0143d 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -208,18 +208,17 @@ repos:
           - --include=requirements/windows.txt
           - requirements/static/pkg/windows.in
 
-# Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.8
-#      - id: pip-tools-compile
-#        alias: compile-pkg-windows-3.8-zmq-requirements
-#        name: Windows Packaging Py3.8 ZeroMQ Requirements
-#        files: ^requirements/((base|zeromq|crypto|windows)\.txt|static/pkg/(windows\.in|py3\.8/windows\.txt))$
-#        pass_filenames: false
-#        args:
-#          - -v
-#          - --py-version=3.8
-#          - --platform=windows
-#          - --include=requirements/windows.txt
-#          - requirements/static/pkg/windows.in
+      - id: pip-tools-compile
+        alias: compile-pkg-windows-3.8-zmq-requirements
+        name: Windows Packaging Py3.8 ZeroMQ Requirements
+        files: ^requirements/((base|zeromq|crypto|windows)\.txt|static/pkg/(windows\.in|py3\.8/windows\.txt))$
+        pass_filenames: false
+        args:
+          - -v
+          - --py-version=3.8
+          - --platform=windows
+          - --include=requirements/windows.txt
+          - requirements/static/pkg/windows.in
 
 # Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.9
 #      - id: pip-tools-compile
@@ -641,20 +640,19 @@ repos:
           - --include=requirements/static/ci/common.in
           - requirements/static/ci/windows.in
 
-# Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.8
-#      - id: pip-tools-compile
-#        alias: compile-ci-windows-py3.8-zmq-requirements
-#        name: Windows CI Py3.8 ZeroMQ Requirements
-#        files: requirements/((base|zeromq|pytest)\.txt|static/((ci|pkg)/(windows|common)\.in|pkg/py3\.8/windows\.txt))$
-#        pass_filenames: false
-#        args:
-#          - -v
-#          - --py-version=3.8
-#          - --platform=windows
-#          - --include=requirements/static/pkg/py{py_version}/windows.txt
-#          - --include=requirements/pytest.txt
-#          - --include=requirements/static/ci/common.in
-#          - requirements/static/ci/windows.in
+      - id: pip-tools-compile
+        alias: compile-ci-windows-py3.8-zmq-requirements
+        name: Windows CI Py3.8 ZeroMQ Requirements
+        files: requirements/((base|zeromq|pytest)\.txt|static/((ci|pkg)/(windows|common)\.in|pkg/py3\.8/windows\.txt))$
+        pass_filenames: false
+        args:
+          - -v
+          - --py-version=3.8
+          - --platform=windows
+          - --include=requirements/static/pkg/py{py_version}/windows.txt
+          - --include=requirements/pytest.txt
+          - --include=requirements/static/ci/common.in
+          - requirements/static/ci/windows.in
 
 # Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.9
 #      - id: pip-tools-compile
@@ -698,20 +696,19 @@ repos:
           - --out-prefix=windows
           - requirements/static/ci/crypto.in
 
-# Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.8
-#      - id: pip-tools-compile
-#        alias: compile-ci-windows-crypto-py3.8-requirements
-#        name: Windows CI Py3.8 Crypto Requirements
-#        files: ^requirements/(crypto\.txt|static/ci/crypto\.in)$
-#        pass_filenames: false
-#        args:
-#          - -v
-#          - --py-version=3.8
-#          - --platform=windows
-#          - --out-prefix=windows
-#          - requirements/static/ci/crypto.in
+      - id: pip-tools-compile
+        alias: compile-ci-windows-crypto-py3.8-requirements
+        name: Windows CI Py3.8 Crypto Requirements
+        files: ^requirements/(crypto\.txt|static/ci/crypto\.in)$
+        pass_filenames: false
+        args:
+          - -v
+          - --py-version=3.8
+          - --platform=windows
+          - --out-prefix=windows
+          - requirements/static/ci/crypto.in
 
-# Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.8
+# Commented out since pywin32 and pymssql do not have packages or support for Py >= 3.9
 #      - id: pip-tools-compile
 #        alias: compile-ci-windows-crypto-py3.9-requirements
 #        name: Windows CI Py3.9 Crypto Requirements
diff --git a/pkg/windows/modules/get-settings.psm1 b/pkg/windows/modules/get-settings.psm1
index aa1ca2c9ca1..7c132616ad9 100644
--- a/pkg/windows/modules/get-settings.psm1
+++ b/pkg/windows/modules/get-settings.psm1
@@ -83,12 +83,18 @@ Function Get-Settings {
 
         # DLL's for 64 bit Windows
         $64bitDLLs = @{
+            "Libeay"     = "libeay32.dll"
+            "SSLeay"     = "ssleay32.dll"
+            "OpenSSLLic" = "OpenSSL_License.txt"
             "Libsodium"  = "libsodium/1.0.18/libsodium.dll"
         }
         $ini.Add("64bitDLLs", $64bitDLLs)
 
         # DLL's for 32 bit Windows
         $32bitDLLs = @{
+            "Libeay"     = "libeay32.dll"
+            "SSLeay"     = "ssleay32.dll"
+            "OpenSSLLic" = "OpenSSL_License.txt"
             "Libsodium"  = "libsodium/1.0.18/libsodium.dll"
         }
         $ini.Add("32bitDLLs", $32bitDLLs)
diff --git a/setup.py b/setup.py
index 1473056ef3d..f8ffe7ef42d 100755
--- a/setup.py
+++ b/setup.py
@@ -504,7 +504,11 @@ class DownloadWindowsDlls(Command):
         url = "https://repo.saltstack.com/windows/dependencies/{bits}/{fname}"
         dest = os.path.join(os.path.dirname(sys.executable), "{fname}")
         with indent_log():
-            for fname in ("libsodium/1.0.18/libsodium.dll",):
+            for fname in (
+                "ssleay32.dll",
+                "libeay32.dll",
+                "libsodium/1.0.18/libsodium.dll",
+            ):
                 # See if the library is already on the system
                 if find_library(fname):
                     continue