diff --git a/.github/workflows/validate_pyinstaller.yml b/.github/workflows/validate_pyinstaller.yml
index 8370328b5d..ab0394ff5d 100644
--- a/.github/workflows/validate_pyinstaller.yml
+++ b/.github/workflows/validate_pyinstaller.yml
@@ -38,9 +38,6 @@ jobs:
       fail-fast: false
     steps:
       - uses: actions/checkout@v3
-      - uses: actions/setup-python@v4
-        with:
-          python-version: "3.7"
       - name: Build PyInstaller
         run: |
           chmod +x ./installer/pyinstaller/build-mac.sh
diff --git a/Makefile b/Makefile
index c69818162d..ecfa78abcf 100644
--- a/Makefile
+++ b/Makefile
@@ -65,7 +65,7 @@ update-reproducible-linux-reqs:
 	venv-update-reproducible-linux/bin/pip-compile --generate-hashes --allow-unsafe -o requirements/reproducible-linux.txt
 
 update-reproducible-mac-reqs:
-	python3.7 -m venv venv-update-reproducible-mac
+	python3.11 -m venv venv-update-reproducible-mac
 	venv-update-reproducible-mac/bin/pip install --upgrade pip-tools pip
 	venv-update-reproducible-mac/bin/pip install -r requirements/base.txt
 	venv-update-reproducible-mac/bin/pip-compile --generate-hashes --allow-unsafe -o requirements/reproducible-mac.txt
diff --git a/installer/pyinstaller/build-mac.sh b/installer/pyinstaller/build-mac.sh
old mode 100644
new mode 100755
index eafcb14f31..5697e24ae7
--- a/installer/pyinstaller/build-mac.sh
+++ b/installer/pyinstaller/build-mac.sh
@@ -30,11 +30,11 @@ if [ "$python_library_zip_filename" = "" ]; then
 fi
 
 if [ "$openssl_version" = "" ]; then
-    openssl_version="1.1.1o";
+    openssl_version="1.1.1t";
 fi
 
 if [ "$python_version" = "" ]; then
-    python_version="3.8.13";
+    python_version="3.11.3";
 fi
 
 if ! [ "$build_binary_name" = "" ]; then
@@ -71,8 +71,20 @@ echo "Copying Source"
 cp -r ../[!.]* ./src
 cp -r ./src/* ./output/aws-sam-cli-src
 
-echo "Removing CI Scripts"
+echo "Removing CI Scripts and other files/direcories not needed"
 rm -vf ./output/aws-sam-cli-src/appveyor*.yml
+rm -rf ./output/aws-sam-cli-src/tests
+rm -rf ./output/aws-sam-cli-src/designs
+rm -rf ./output/aws-sam-cli-src/docs
+rm -rf ./output/aws-sam-cli-src/media
+rm -rf ./output/aws-sam-cli-src/Make.ps1
+rm -rf ./output/aws-sam-cli-src/CODEOWNERS
+rm -rf ./output/aws-sam-cli-src/CODE_OF_CONDUCT.md
+rm -rf ./output/aws-sam-cli-src/CONTRIBUTING.md
+rm -rf ./output/aws-sam-cli-src/DESIGN.md
+rm -rf ./output/aws-sam-cli-src/Makefile
+rm -rf ./output/aws-sam-cli-src/mypy.ini
+rm -rf ./output/aws-sam-cli-src/pytest.ini
 
 echo "Installing Python"
 curl "https://www.python.org/ftp/python/${python_version}/Python-${python_version}.tgz" --output python.tgz
@@ -84,7 +96,7 @@ sudo make install
 cd ..
 
 echo "Installing Python Libraries"
-/usr/local/bin/python3.8 -m venv venv
+/usr/local/bin/python3.11 -m venv venv
 ./venv/bin/pip install --upgrade pip
 ./venv/bin/pip install -r src/requirements/reproducible-mac.txt
 
diff --git a/requirements/reproducible-mac.txt b/requirements/reproducible-mac.txt
index 14dfaf2c06..4971ae1661 100644
--- a/requirements/reproducible-mac.txt
+++ b/requirements/reproducible-mac.txt
@@ -1,5 +1,5 @@
 #
-# This file is autogenerated by pip-compile with Python 3.7
+# 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-mac.txt
@@ -25,24 +25,6 @@ aws-sam-translator==1.68.0 \
     # 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
@@ -271,19 +253,6 @@ idna==3.4 \
     --hash=sha256:814f528e8dead7d329833b91c5faa87d60bf71824cd12a7530b5526063d02cb4 \
     --hash=sha256:90b77e79eaa3eba6de819a0c442c0b4ceefc341a7a2ab77d7562bf49f425c5c2
     # via requests
-importlib-metadata==6.1.0 \
-    --hash=sha256:43ce9281e097583d758c2c708c4376371261a02c34682491a8e98352365aad20 \
-    --hash=sha256:ff80f3b5394912eb1b108fcfd444dc78b7f1f3e16b16188054bd01cb9cb86f09
-    # via
-    #   attrs
-    #   click
-    #   flask
-    #   jsonpickle
-    #   jsonschema
-importlib-resources==5.12.0 \
-    --hash=sha256:4be82589bf5c1d7999aedf2a45159d10cb3ca4f19b2271f8792bc8e6da7b22f6 \
-    --hash=sha256:7b1deeebbf351c7578e09bf2f63fa2ce8b5ffec296e0d349139d43cca061a81a
-    # via jsonschema
 itsdangerous==2.1.2 \
     --hash=sha256:2c2349112351b88699d8d4b6b075022c0808887cb7ad10069318a8b0bc88db44 \
     --hash=sha256:5dbbc68b317e5e42f327f9021763545dc3fc3bfe22e6deb96aaf1fc38874156a
@@ -408,10 +377,6 @@ 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
@@ -649,44 +614,6 @@ ruamel-yaml==0.17.21 \
     --hash=sha256:742b35d3d665023981bd6d16b3d24248ce5df75fdb4e2924e93a05c1f8b61ca7 \
     --hash=sha256:8b7ce697a2f212752a35c1ac414471dc16c424c9573be4926b56ff3f5d23b7af
     # via aws-sam-cli (setup.py)
-ruamel-yaml-clib==0.2.7 \
-    --hash=sha256:045e0626baf1c52e5527bd5db361bc83180faaba2ff586e763d3d5982a876a9e \
-    --hash=sha256:15910ef4f3e537eea7fe45f8a5d19997479940d9196f357152a09031c5be59f3 \
-    --hash=sha256:184faeaec61dbaa3cace407cffc5819f7b977e75360e8d5ca19461cd851a5fc5 \
-    --hash=sha256:1f08fd5a2bea9c4180db71678e850b995d2a5f4537be0e94557668cf0f5f9497 \
-    --hash=sha256:2aa261c29a5545adfef9296b7e33941f46aa5bbd21164228e833412af4c9c75f \
-    --hash=sha256:3110a99e0f94a4a3470ff67fc20d3f96c25b13d24c6980ff841e82bafe827cac \
-    --hash=sha256:3243f48ecd450eddadc2d11b5feb08aca941b5cd98c9b1db14b2fd128be8c697 \
-    --hash=sha256:370445fd795706fd291ab00c9df38a0caed0f17a6fb46b0f607668ecb16ce763 \
-    --hash=sha256:40d030e2329ce5286d6b231b8726959ebbe0404c92f0a578c0e2482182e38282 \
-    --hash=sha256:41d0f1fa4c6830176eef5b276af04c89320ea616655d01327d5ce65e50575c94 \
-    --hash=sha256:4a4d8d417868d68b979076a9be6a38c676eca060785abaa6709c7b31593c35d1 \
-    --hash=sha256:4b3a93bb9bc662fc1f99c5c3ea8e623d8b23ad22f861eb6fce9377ac07ad6072 \
-    --hash=sha256:5bc0667c1eb8f83a3752b71b9c4ba55ef7c7058ae57022dd9b29065186a113d9 \
-    --hash=sha256:721bc4ba4525f53f6a611ec0967bdcee61b31df5a56801281027a3a6d1c2daf5 \
-    --hash=sha256:763d65baa3b952479c4e972669f679fe490eee058d5aa85da483ebae2009d231 \
-    --hash=sha256:7bdb4c06b063f6fd55e472e201317a3bb6cdeeee5d5a38512ea5c01e1acbdd93 \
-    --hash=sha256:8831a2cedcd0f0927f788c5bdf6567d9dc9cc235646a434986a852af1cb54b4b \
-    --hash=sha256:91a789b4aa0097b78c93e3dc4b40040ba55bef518f84a40d4442f713b4094acb \
-    --hash=sha256:92460ce908546ab69770b2e576e4f99fbb4ce6ab4b245345a3869a0a0410488f \
-    --hash=sha256:99e77daab5d13a48a4054803d052ff40780278240a902b880dd37a51ba01a307 \
-    --hash=sha256:a234a20ae07e8469da311e182e70ef6b199d0fbeb6c6cc2901204dd87fb867e8 \
-    --hash=sha256:a7b301ff08055d73223058b5c46c55638917f04d21577c95e00e0c4d79201a6b \
-    --hash=sha256:be2a7ad8fd8f7442b24323d24ba0b56c51219513cfa45b9ada3b87b76c374d4b \
-    --hash=sha256:bf9a6bc4a0221538b1a7de3ed7bca4c93c02346853f44e1cd764be0023cd3640 \
-    --hash=sha256:c3ca1fbba4ae962521e5eb66d72998b51f0f4d0f608d3c0347a48e1af262efa7 \
-    --hash=sha256:d000f258cf42fec2b1bbf2863c61d7b8918d31ffee905da62dede869254d3b8a \
-    --hash=sha256:d5859983f26d8cd7bb5c287ef452e8aacc86501487634573d260968f753e1d71 \
-    --hash=sha256:d5e51e2901ec2366b79f16c2299a03e74ba4531ddcfacc1416639c557aef0ad8 \
-    --hash=sha256:da538167284de58a52109a9b89b8f6a53ff8437dd6dc26d33b57bf6699153122 \
-    --hash=sha256:debc87a9516b237d0466a711b18b6ebeb17ba9f391eb7f91c649c5c4ec5006c7 \
-    --hash=sha256:df5828871e6648db72d1c19b4bd24819b80a755c4541d3409f0f7acd0f335c80 \
-    --hash=sha256:ecdf1a604009bd35c674b9225a8fa609e0282d9b896c03dd441a91e5f53b534e \
-    --hash=sha256:efa08d63ef03d079dcae1dfe334f6c8847ba8b645d08df286358b1f5293d24ab \
-    --hash=sha256:f01da5790e95815eb5a8a138508c01c758e5f5bc0ce4286c4f7028b8dd7ac3d0 \
-    --hash=sha256:f34019dced51047d6f70cb9383b2ae2853b7fc4dce65129a5acd49f4f9256646 \
-    --hash=sha256:f6d3d39611ac2e4f62c3128a9eed45f19a6608670c5a2f4f07f24e8de3441d38
-    # via ruamel-yaml
 s3transfer==0.6.0 \
     --hash=sha256:06176b74f3a15f61f1b4f25a1fc29a4429040b7647133a463da8fa5bd28d5ecd \
     --hash=sha256:2ed07d3866f523cc561bf4a00fc5535827981b117dd7876f036b0c1aca42c947
@@ -723,14 +650,9 @@ typing-extensions==4.4.0 \
     --hash=sha256:1511434bb92bf8dd198c12b1cc812e800d4181cfcb867674e0f8279cc93087aa \
     --hash=sha256:16fa4864408f655d35ec496218b85f79b3437c829e93320c7c9215ccfd92489e
     # via
-    #   arrow
     #   aws-sam-cli (setup.py)
     #   aws-sam-translator
-    #   importlib-metadata
-    #   jsonschema
-    #   markdown-it-py
     #   pydantic
-    #   rich
 tzlocal==3.0 \
     --hash=sha256:c736f2540713deb5938d789ca7c3fc25391e9a20803f05b60ec64987cf086559 \
     --hash=sha256:f4e6e36db50499e0d92f79b67361041f048e2609d166e93456b50746dc4aef12
@@ -774,12 +696,6 @@ wheel==0.40.0 \
     --hash=sha256:cd1196f3faee2b31968d626e1731c94f99cbdb67cf5a46e4f5656cbee7738873 \
     --hash=sha256:d236b20e7cb522daf2390fa84c55eea81c5c30190f90f29ae2ca1ad8355bf247
     # via aws-lambda-builders
-zipp==3.15.0 \
-    --hash=sha256:112929ad649da941c23de50f356a2b5570c954b65150642bccdd66bf194d224b \
-    --hash=sha256:48904fc76a60e542af151aded95726c1a5c34ed43ab4134b597665c86d7ad556
-    # via
-    #   importlib-metadata
-    #   importlib-resources
 
 # The following packages are considered to be unsafe in a requirements file:
 setuptools==67.7.2 \