diff --git a/.github/workflows/integration-test.yml b/.github/workflows/integration-test.yml
index 7ae62ef1de..751ed9f0e0 100644
--- a/.github/workflows/integration-test.yml
+++ b/.github/workflows/integration-test.yml
@@ -79,6 +79,7 @@ jobs:
     with:
       ContainerRepositoryNameAndTag: "cwagent-integration-test:${{ github.sha }}"
       BucketKey: "integration-test/binary/${{ github.sha }}"
+      PackageBucketKey: "integration-test/packaging/${{ github.sha }}"
 
   BuildAndUploadITAR:
     uses: ./.github/workflows/test-build.yml
diff --git a/.github/workflows/nightly-build.yml b/.github/workflows/nightly-build.yml
index 89455f5761..3716d9cdd0 100644
--- a/.github/workflows/nightly-build.yml
+++ b/.github/workflows/nightly-build.yml
@@ -41,3 +41,4 @@ jobs:
     with:
       ContainerRepositoryNameAndTag: "nightly-build:latest"
       BucketKey: "nightly-build/latest"
+      PackageBucketKey: "nightly-build/latest"
diff --git a/.github/workflows/soak-test.yml b/.github/workflows/soak-test.yml
index 0239941e52..abb9529cdc 100644
--- a/.github/workflows/soak-test.yml
+++ b/.github/workflows/soak-test.yml
@@ -58,6 +58,7 @@ jobs:
     with:
       ContainerRepositoryNameAndTag: "cwagent-integration-test:${{ github.sha }}"
       BucketKey: "integration-test/binary/${{ github.sha }}"
+      PackageBucketKey: "integration-test/packaging/${{ github.sha }}"
 
   DeploySoakTest:
     name: "DeploySoakTest"
diff --git a/.github/workflows/test-build-docker.yml b/.github/workflows/test-build-docker.yml
index ef5d71c8d9..abfeb60fec 100644
--- a/.github/workflows/test-build-docker.yml
+++ b/.github/workflows/test-build-docker.yml
@@ -22,6 +22,10 @@ on:
         description: "S3 URI to upload artifacts into."
         required: true
         type: string
+      PackageBucketKey:
+        description: "Integration tests put the MSI and PKG in a different bucket path than the binaries."
+        required: true
+        type: string
   workflow_call:
     inputs:
       ContainerRepositoryNameAndTag:
@@ -38,6 +42,10 @@ on:
         description: "S3 URI to upload artifacts into."
         required: true
         type: string
+      PackageBucketKey:
+        description: "Integration tests put the MSI and PKG in a different bucket path than the binaries."
+        required: true
+        type: string
 
 jobs:
   MakeBinary:
@@ -86,7 +94,26 @@ jobs:
           aws s3 cp s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.BucketKey }}/linux/amd64/amazon-cloudwatch-agent.deb amd64/amazon-cloudwatch-agent.deb
           aws s3 cp s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.BucketKey }}/linux/arm64/amazon-cloudwatch-agent.deb arm64/amazon-cloudwatch-agent.deb
 
-      - name: Build Cloudwatch Agent Image
+      - name: Get ECR Repo name
+        id: repo_name
+        env:
+          ContainerRepositoryNameAndTag: ${{ inputs.ContainerRepositoryNameAndTag }}
+        run: |
+          RepoName=`echo $ContainerRepositoryNameAndTag | awk -F: '{print $1}'`
+          echo "::set-output name=ContainerRepositoryName::$RepoName"
+
+      - name: Build Cloudwatch Agent Image amd64
+        uses: docker/build-push-action@v4
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_container.outputs.cache-hit == false
+        with:
+          file: amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localdeb/Dockerfile
+          context: .
+          push: true
+          tags: |
+            ${{ steps.login-ecr.outputs.registry }}/${{ steps.repo_name.outputs.ContainerRepositoryName }}:linux-amd64
+          platforms: linux/amd64
+
+      - name: Build Cloudwatch Agent Image arm64
         uses: docker/build-push-action@v4
         if: contains(inputs.BucketKey, 'test') == false || steps.cached_container.outputs.cache-hit == false
         with:
@@ -94,5 +121,318 @@ jobs:
           context: .
           push: true
           tags: |
-            ${{ steps.login-ecr.outputs.registry }}/${{ inputs.ContainerRepositoryNameAndTag }}
-          platforms: linux/amd64, linux/arm64
\ No newline at end of file
+            ${{ steps.login-ecr.outputs.registry }}/${{ steps.repo_name.outputs.ContainerRepositoryName }}:linux-arm64
+          platforms: linux/arm64
+
+  MakeMSIZip:
+    name: 'MakeMSIZip'
+    runs-on: ubuntu-latest
+    permissions:
+      id-token: write
+      contents: read
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          repository: ${{env.CWA_GITHUB_TEST_REPO_NAME}}
+
+      - name: Set up Go 1.x
+        uses: actions/setup-go@v4
+        with:
+          go-version: ~1.21.1
+
+      - name: Configure AWS Credentials
+        uses: aws-actions/configure-aws-credentials@v2
+        with:
+          role-to-assume: ${{ secrets.TERRAFORM_AWS_ASSUME_ROLE }}
+          aws-region: us-west-2
+
+      - name: Cache win zip
+        id: cached_win_zip
+        uses: actions/cache@v3
+        with:
+          key: "cached_win_zip_${{ github.sha }}_${{ inputs.PackageBucketKey }}_${{ inputs.Bucket }}_${{ inputs.BucketKey }}"
+          path: go.mod
+
+      - name: Copy binary
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
+        run: |
+          aws s3 cp s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.BucketKey }} . --recursive
+      - name: Unzip
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
+        run: |
+          sudo apt install unzip
+          unzip windows/amd64/amazon-cloudwatch-agent.zip -d windows-agent
+      - name: Create msi dep folder and copy deps
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
+        run: |
+          export version=$(cat CWAGENT_VERSION)
+          echo cw agent version $version
+          mkdir msi_dep
+          cp -r msi/tools/. msi_dep/
+          cp -r windows-agent/amazon-cloudwatch-agent/. msi_dep/
+          go run msi/tools/msiversion/msiversionconverter.go $version msi_dep/amazon-cloudwatch-agent.wxs '<version>'
+          go run msi/tools/msiversion/msiversionconverter.go $version msi_dep/manifest.json __VERSION__
+
+      - name: Zip
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
+        run: |
+          sudo apt install zip
+          zip buildMSI.zip msi_dep/*
+
+      - name: Upload zip
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
+        run: aws s3 cp buildMSI.zip s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.BucketKey }}/buildMSI.zip
+
+  BuildMSI-2022:
+    name: 'BuildMSI-2022'
+    runs-on: windows-latest
+    needs: [ MakeMSIZip ]
+    permissions:
+      id-token: write
+      contents: read
+    steps:
+      - uses: actions/checkout@v3
+
+      - name: Configure AWS Credentials
+        uses: aws-actions/configure-aws-credentials@v2
+        with:
+          role-to-assume: ${{ secrets.TERRAFORM_AWS_ASSUME_ROLE }}
+          aws-region: us-west-2
+
+      - name: Cache msi
+        id: cached_msi
+        uses: actions/cache@v3
+        with:
+          key: "cached_msi_${{ github.sha }}"
+          path: go.mod
+
+      # Using the env variable returns "" for bucket name thus use the secret
+      - name: Copy msi
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: aws s3 cp s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.BucketKey }}/buildMSI.zip .
+
+      - name: Create msi
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: |
+          curl -OLS https://github.com/wixtoolset/wix3/releases/download/wix314rtm/wix314.exe
+          .\wix314.exe /install /quiet /norestart
+          $wixToolsetBinPath = ";C:\Program Files (x86)\WiX Toolset v3.14\bin;"
+          $env:PATH = $env:PATH + $wixToolsetBinPath
+          Expand-Archive buildMSI.zip -Force
+          cd buildMSI/msi_dep
+          .\create_msi.ps1 "nosha" ${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.PackageBucketKey }}
+
+      - name: clean ecr login credential cache
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run : |
+          echo '{"auths": {"https://index.docker.io/v1/": {}}, "HttpHeaders": { "User-Agent": "Docker-Client/19.03.12 (windows)"}}' > ~/.docker/config.json
+
+      - name: Login ECR
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        id: login-ecr
+        uses: aws-actions/amazon-ecr-login@v1
+
+      # Build dir is ignored in our .dockerignore thus need to copy to another dir.
+      - name: Copy Binary For Agent Image Build
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: |
+          pwd
+          mkdir amd64
+          cp -r buildMSI/msi_dep/amazon-cloudwatch-agent.msi amd64/
+
+      - name: Get ECR Repo name
+        id: repo_name
+        env:
+          ContainerRepositoryNameAndTag: ${{ inputs.ContainerRepositoryNameAndTag }}
+        run: |
+          $splitArray = $env:ContainerRepositoryNameAndTag.Split(":")[0]
+          Write-Output "::set-output name=ContainerRepositoryName::$splitArray"
+
+      - name: Build Windows Cloudwatch Agent Image
+        env:
+          REGISTRY: ${{ steps.login-ecr.outputs.registry }}
+          REPOSITORY: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:2022
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: |
+          Write-Output "$env:REGISTRY/$env:REPOSITORY"
+          docker build --platform windows/amd64 -f ./amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localmsi/Dockerfile.Windows . -t $env:REGISTRY/$env:REPOSITORY
+          docker push $env:REGISTRY/$env:REPOSITORY
+
+  BuildMSI-2019:
+    name: 'BuildMSI-2019'
+    runs-on: windows-2019
+    needs: [MakeMSIZip]
+    permissions:
+      id-token: write
+      contents: read
+    steps:
+      - uses: actions/checkout@v3
+
+      - name: Configure AWS Credentials
+        uses: aws-actions/configure-aws-credentials@v2
+        with:
+          role-to-assume: ${{ secrets.TERRAFORM_AWS_ASSUME_ROLE }}
+          aws-region: us-west-2
+
+      - name: Cache msi
+        id: cached_msi
+        uses: actions/cache@v3
+        with:
+          key: "cached_msi_${{ github.sha }}"
+          path: go.mod
+
+      # Using the env variable returns "" for bucket name thus use the secret
+      - name: Copy msi
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: aws s3 cp s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.BucketKey }}/buildMSI.zip .
+
+      - name: Create msi
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run : |
+          curl -OLS https://github.com/wixtoolset/wix3/releases/download/wix314rtm/wix314.exe
+          .\wix314.exe /install /quiet /norestart
+          $wixToolsetBinPath = ";C:\Program Files (x86)\WiX Toolset v3.14\bin;"
+          $env:PATH = $env:PATH + $wixToolsetBinPath
+          Expand-Archive buildMSI.zip -Force
+          cd buildMSI/msi_dep
+          .\create_msi.ps1 "nosha" ${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.PackageBucketKey }}
+
+      - name: clean ecr login credential cache
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run : |
+          echo '{"auths": {"https://index.docker.io/v1/": {}}, "HttpHeaders": { "User-Agent": "Docker-Client/19.03.12 (windows)"}}' > ~/.docker/config.json
+
+      - name: Login ECR
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        id: login-ecr
+        uses: aws-actions/amazon-ecr-login@v1
+
+      # Build dir is ignored in our .dockerignore thus need to copy to another dir.
+      - name: Copy Binary For Agent Image Build
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: |
+          pwd
+          mkdir amd64
+          cp -r buildMSI/msi_dep/amazon-cloudwatch-agent.msi amd64/
+
+      - name: Get ECR Repo name
+        id: repo_name
+        env:
+          ContainerRepositoryNameAndTag: ${{ inputs.ContainerRepositoryNameAndTag }}
+        run: |
+          $splitArray = $env:ContainerRepositoryNameAndTag.Split(":")[0]
+          Write-Output "::set-output name=ContainerRepositoryName::$splitArray"
+
+      - name: Build Windows Cloudwatch Agent Image
+        env:
+          REGISTRY: ${{ steps.login-ecr.outputs.registry }}
+          REPOSITORY: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:2019
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
+        run: |
+          Write-Output "$env:REGISTRY/$env:REPOSITORY"
+          docker build --platform windows/amd64 -f ./amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localmsi/Dockerfile.Windows --build-arg IMAGE_TAG=ltsc2019 . -t $env:REGISTRY/$env:REPOSITORY
+          docker push $env:REGISTRY/$env:REPOSITORY
+
+  CreateContainerManifest:
+    name: 'CreateManifest'
+    needs: ['BuildMSI-2019', 'BuildMSI-2022', 'MakeBinary']
+    runs-on: ubuntu-latest
+    permissions:
+      id-token: write
+      contents: read
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          fetch-depth: 0
+
+      - name: Install rpm
+        run: sudo apt install rpm
+
+      - name: Configure AWS Credentials
+        uses: aws-actions/configure-aws-credentials@v2
+        with:
+          role-to-assume: ${{ secrets.TERRAFORM_AWS_ASSUME_ROLE }}
+          aws-region: us-west-2
+
+      - name: Login ECR
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_binaries.outputs.cache-hit == false
+        id: login-ecr
+        uses: aws-actions/amazon-ecr-login@v1
+
+      - name: Set up Docker Buildx
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_binaries.outputs.cache-hit == false
+        uses: docker/setup-buildx-action@v1
+
+      - name: Get ECR Repo name
+        id: repo_name
+        env:
+          ContainerRepositoryNameAndTag: ${{ inputs.ContainerRepositoryNameAndTag }}
+        run: |
+          RepoName=`echo $ContainerRepositoryNameAndTag | awk -F: '{print $1}'`
+          echo "::set-output name=ContainerRepositoryName::$RepoName"
+
+      - name: Create manifest and push
+        env:
+          REGISTRY: ${{ steps.login-ecr.outputs.registry }}
+          OrigREPOSITORY: ${{ inputs.ContainerRepositoryNameAndTag }}
+          REPOSITORY: ${{ steps.repo_name.outputs.ContainerRepositoryName }}
+          REPOSITORYWindows: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:windows
+          REPO2022: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:2022
+          REPO2019: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:2019
+          REPOLinuxAmd: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:linux-amd64
+          REPOLinuxArm: ${{ steps.repo_name.outputs.ContainerRepositoryName }}:linux-arm64
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_binaries.outputs.cache-hit == false
+        run: |
+          docker manifest create $REGISTRY/$REPOSITORYWindows --amend $REGISTRY/$REPO2022 --amend $REGISTRY/$REPO2019
+          docker manifest push $REGISTRY/$REPOSITORYWindows
+
+          docker buildx imagetools inspect --raw $REGISTRY/$REPOLinuxAmd | jq '.manifests[0]' > linux-amd.json
+          docker buildx imagetools inspect --raw $REGISTRY/$REPOLinuxArm | jq '.manifests[0]' > linux-arm.json
+          docker buildx imagetools inspect --raw $REGISTRY/$REPOSITORYWindows | jq '.manifests[0]' > 2019.json
+          docker buildx imagetools inspect --raw $REGISTRY/$REPOSITORYWindows | jq '.manifests[1]' > 2022.json
+
+          docker buildx imagetools create -f linux-amd.json -f linux-arm.json -f 2019.json -f 2022.json --tag $REGISTRY/$OrigREPOSITORY
+
+  #GH actions set up gpg only works on ubuntu as of this commit date
+  GPGSignWindowsPackage:
+    name: 'GPGSignWindowsPackage'
+    runs-on: ubuntu-latest
+    needs: [ BuildMSI-2022 ]
+    permissions:
+      id-token: write
+      contents: read
+    steps:
+      - uses: actions/checkout@v3
+
+      - name: Configure AWS Credentials
+        uses: aws-actions/configure-aws-credentials@v2
+        with:
+          role-to-assume: ${{ secrets.TERRAFORM_AWS_ASSUME_ROLE }}
+          aws-region: us-west-2
+
+      - name: Cache sig
+        id: cached_sig
+        uses: actions/cache@v3
+        with:
+          key: "cached_sig_${{ github.sha }}"
+          path: go.mod
+
+      - name: Download from s3
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_sig.outputs.cache-hit == false
+        run: |
+          mkdir -p packages/amd64
+          mkdir packages/arm64
+          aws s3 cp s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.PackageBucketKey }}/amazon-cloudwatch-agent.msi ./packages/amazon-cloudwatch-agent.msi
+      - name: Import GPG Key
+        uses: crazy-max/ghaction-import-gpg@v5
+        with:
+          gpg_private_key: ${{ secrets.GPG_PRIVATE_KEY }}
+          passphrase: ${{ secrets.PASSPHRASE }}
+
+      - name: Sign Build Files
+        run: for f in $(find packages/); do if [ ! -d $f ]; then echo "Signing file $f" && gpg --detach-sign $f ; fi ; done
+
+      - name: Upload to s3
+        if: contains(inputs.BucketKey, 'test') == false || steps.cached_sig.outputs.cache-hit == false
+        run: |
+          aws s3 cp packages/amazon-cloudwatch-agent.msi.sig s3://${{ secrets.S3_INTEGRATION_BUCKET }}/${{ inputs.PackageBucketKey }}/amazon-cloudwatch-agent.msi.sig
diff --git a/.github/workflows/test-build-packages.yml b/.github/workflows/test-build-packages.yml
index 9ffb19d33d..d42960bcd7 100644
--- a/.github/workflows/test-build-packages.yml
+++ b/.github/workflows/test-build-packages.yml
@@ -60,65 +60,6 @@ on:
         type: string
 
 jobs:
-  MakeMSIZip:
-    name: 'MakeMSIZip'
-    runs-on: ubuntu-latest
-    permissions:
-      id-token: write
-      contents: read
-    steps:
-      - uses: actions/checkout@v3
-        with:
-          repository: ${{env.CWA_GITHUB_TEST_REPO_NAME}}
-
-      - name: Set up Go 1.x
-        uses: actions/setup-go@v4
-        with:
-          go-version: ~1.21.1
-
-      - name: Configure AWS Credentials
-        uses: aws-actions/configure-aws-credentials@v2
-        with:
-          role-to-assume: ${{ inputs.TerraformAWSAssumeRole }}
-          aws-region: ${{ inputs.Region }}
-
-      - name: Cache win zip
-        id: cached_win_zip
-        uses: actions/cache@v3
-        with:
-          key: "cached_win_zip_${{ github.sha }}_${{ inputs.PackageBucketKey }}_${{ inputs.Bucket }}_${{ inputs.BucketKey }}"
-          path: go.mod
-
-      - name: Copy binary
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
-        run: |
-          aws s3 cp s3://${{ inputs.Bucket }}/${{ inputs.BucketKey }} . --recursive
-      - name: Unzip
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
-        run: |
-          sudo apt install unzip
-          unzip windows/amd64/amazon-cloudwatch-agent.zip -d windows-agent
-      - name: Create msi dep folder and copy deps
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
-        run: |
-          export version=$(cat CWAGENT_VERSION)
-          echo cw agent version $version
-          mkdir msi_dep
-          cp -r msi/tools/. msi_dep/
-          cp -r windows-agent/amazon-cloudwatch-agent/. msi_dep/
-          go run msi/tools/msiversion/msiversionconverter.go $version msi_dep/amazon-cloudwatch-agent.wxs '<version>'
-          go run msi/tools/msiversion/msiversionconverter.go $version msi_dep/manifest.json __VERSION__
-
-      - name: Zip
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
-        run: |
-          sudo apt install zip
-          zip buildMSI.zip msi_dep/*
-
-      - name: Upload zip
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_win_zip.outputs.cache-hit == false
-        run: aws s3 cp buildMSI.zip s3://${{ inputs.Bucket }}/${{ inputs.BucketKey }}/buildMSI.zip
-
   MakeMacPkg:
     name: 'MakeMacPkg'
     runs-on: macos-11
@@ -194,50 +135,11 @@ jobs:
           cd arm64
           ./create_pkg.sh ${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }} "nosha" arm64
 
-  BuildMSI:
-    name: 'BuildMSI'
-    runs-on: windows-latest
-    needs: [ MakeMSIZip ]
-    permissions:
-      id-token: write
-      contents: read
-    steps:
-      - uses: actions/checkout@v3
-
-      - name: Configure AWS Credentials
-        uses: aws-actions/configure-aws-credentials@v2
-        with:
-          role-to-assume: ${{ inputs.TerraformAWSAssumeRole }}
-          aws-region: ${{ inputs.Region }}
-
-      - name: Cache msi
-        id: cached_msi
-        uses: actions/cache@v3
-        with:
-          key: "cached_msi_${{ github.sha }}"
-          path: go.mod
-
-      # Using the env variable returns "" for bucket name thus use the secret
-      - name: Copy msi
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
-        run: aws s3 cp s3://${{ inputs.Bucket }}/${{ inputs.BucketKey }}/buildMSI.zip .
-
-      - name: Create msi
-        if: contains(inputs.BucketKey, 'test') == false || steps.cached_msi.outputs.cache-hit == false
-        run: |
-          curl -OLS https://github.com/wixtoolset/wix3/releases/download/wix3111rtm/wix311.exe
-          .\wix311.exe /install /quiet /norestart
-          $wixToolsetBinPath = ";C:\Program Files (x86)\WiX Toolset v3.11\bin;"
-          $env:PATH = $env:PATH + $wixToolsetBinPath
-          Expand-Archive buildMSI.zip -Force
-          cd buildMSI/msi_dep
-          .\create_msi.ps1 "nosha" ${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}
-
   #GH actions set up gpg only works on ubuntu as of this commit date
-  GPGSignMacAndWindowsPackage:
-    name: 'SignMacAndWindowsPackage'
+  GPGSignMacPackage:
+    name: 'GPGSignMacPackage'
     runs-on: ubuntu-latest
-    needs: [ BuildMSI, MakeMacPkg ]
+    needs: [  MakeMacPkg ]
     permissions:
       id-token: write
       contents: read
@@ -262,7 +164,6 @@ jobs:
         run: |
           mkdir -p packages/amd64
           mkdir packages/arm64
-          aws s3 cp s3://${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}/amazon-cloudwatch-agent.msi ./packages/amazon-cloudwatch-agent.msi
           aws s3 cp s3://${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}/amd64/amazon-cloudwatch-agent.pkg ./packages/amd64/amazon-cloudwatch-agent.pkg
           aws s3 cp s3://${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}/arm64/amazon-cloudwatch-agent.pkg ./packages/arm64/amazon-cloudwatch-agent.pkg
       - name: Import GPG Key
@@ -277,6 +178,5 @@ jobs:
       - name: Upload to s3
         if: contains(inputs.BucketKey, 'test') == false || steps.cached_sig.outputs.cache-hit == false
         run: |
-          aws s3 cp packages/amazon-cloudwatch-agent.msi.sig s3://${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}/amazon-cloudwatch-agent.msi.sig
           aws s3 cp packages/amd64/amazon-cloudwatch-agent.pkg.sig s3://${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}/amd64/amazon-cloudwatch-agent.pkg.sig
           aws s3 cp packages/arm64/amazon-cloudwatch-agent.pkg.sig s3://${{ inputs.Bucket }}/${{ inputs.PackageBucketKey }}/arm64/amazon-cloudwatch-agent.pkg.sig
diff --git a/Makefile b/Makefile
index 88dbbaf30c..986a2de49b 100644
--- a/Makefile
+++ b/Makefile
@@ -30,6 +30,7 @@ IMAGE_REPO = cloudwatch-agent
 IMAGE_TAG = $(VERSION)
 IMAGE = $(IMAGE_REGISTRY)/$(IMAGE_REPO):$(IMAGE_TAG)
 DOCKER_BUILD_FROM_SOURCE = docker build -t $(IMAGE) -f ./amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/source/Dockerfile
+DOCKER_WINDOWS_BUILD_FROM_SOURCE = docker build -t $(IMAGE) -f ./amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/source/Dockerfile.Windows
 
 CW_AGENT_IMPORT_PATH=github.com/aws/amazon-cloudwatch-agent
 ALL_SRC := $(shell find . -name '*.go' -type f | sort)
@@ -109,6 +110,11 @@ build-for-docker-amd64:
 	$(LINUX_AMD64_BUILD)/start-amazon-cloudwatch-agent github.com/aws/amazon-cloudwatch-agent/cmd/start-amazon-cloudwatch-agent
 	$(LINUX_AMD64_BUILD)/config-translator github.com/aws/amazon-cloudwatch-agent/cmd/config-translator
 
+build-for-docker-windows-amd64:
+	$(WIN_BUILD)/amazon-cloudwatch-agent.exe github.com/aws/amazon-cloudwatch-agent/cmd/amazon-cloudwatch-agent
+	$(WIN_BUILD)/start-amazon-cloudwatch-agent.exe github.com/aws/amazon-cloudwatch-agent/cmd/start-amazon-cloudwatch-agent
+	$(WIN_BUILD)/config-translator.exe github.com/aws/amazon-cloudwatch-agent/cmd/config-translator
+
 build-for-docker-arm64:
 	$(LINUX_ARM64_BUILD)/amazon-cloudwatch-agent github.com/aws/amazon-cloudwatch-agent/cmd/amazon-cloudwatch-agent
 	$(LINUX_ARM64_BUILD)/start-amazon-cloudwatch-agent github.com/aws/amazon-cloudwatch-agent/cmd/start-amazon-cloudwatch-agent
@@ -126,6 +132,13 @@ docker-build-arm64: build-for-docker-arm64
 docker-push:
 	docker push $(IMAGE)
 
+build-for-docker-fast-windows-amd64: build-for-docker-windows-amd64
+	rm -rf tmp
+	mkdir -p tmp/windows_amd64
+	cp build/bin/windows_amd64/* tmp/windows_amd64
+	docker build --platform windows/amd64 -f amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localbin/Dockerfile.Windows . -t amazon-cloudwatch-agent
+	rm -rf tmp
+
 install-goimports:
 	GOBIN=$(TOOLS_BIN_DIR) go install golang.org/x/tools/cmd/goimports
 
@@ -315,3 +328,9 @@ dockerized-build:
 # Use vendor instead of proxy when building w/ vendor folder
 dockerized-build-vendor:
 	$(DOCKER_BUILD_FROM_SOURCE) --build-arg GO111MODULE=off .
+
+.PHONY: dockerized-windows-build
+dockerized-windows-build:
+	$(DOCKER_WINDOWS_BUILD_FROM_SOURCE) .
+	@echo Built image:
+	@echo $(IMAGE)
\ No newline at end of file
diff --git a/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localbin/Dockerfile.Windows b/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localbin/Dockerfile.Windows
new file mode 100644
index 0000000000..2fcd11d577
--- /dev/null
+++ b/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localbin/Dockerfile.Windows
@@ -0,0 +1,22 @@
+# This Dockerfile can be used for building Windows Server 2019, 2022 Container images.
+
+# Build Container image from binary in local
+ARG TAG=ltsc2022
+ARG TARGETARCH=amd64
+ARG CONTAINER_CLOUDWATCHAGENT_PATH=C:\\Program\ Files\\Amazon\\AmazonCloudWatchAgent\\
+ARG CONTAINER_CLOUDWATCHAGENT_DATA_PATH=C:\\ProgramData\\Amazon\\AmazonCloudWatchAgent\\
+
+FROM mcr.microsoft.com/windows/servercore:$TAG as runtime
+
+ARG CONTAINER_CLOUDWATCHAGENT_PATH
+ARG CONTAINER_CLOUDWATCHAGENT_DATA_PATH
+ARG TARGETARCH
+
+RUN Powershell -Command New-Item -ItemType Directory -Path $Env:CONTAINER_CLOUDWATCHAGENT_PATH -Force
+RUN Powershell -Command New-Item -ItemType Directory -Path $Env:CONTAINER_CLOUDWATCHAGENT_DATA_PATH -Force
+WORKDIR $CONTAINER_CLOUDWATCHAGENT_PATH
+
+COPY "./tmp/windows_${TARGETARCH}" $CONTAINER_CLOUDWATCHAGENT_PATH
+
+ENV RUN_IN_CONTAINER="True"
+CMD ["start-amazon-cloudwatch-agent.exe"]
\ No newline at end of file
diff --git a/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localmsi/Dockerfile.Windows b/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localmsi/Dockerfile.Windows
new file mode 100644
index 0000000000..be00aff3dc
--- /dev/null
+++ b/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/localmsi/Dockerfile.Windows
@@ -0,0 +1,20 @@
+# This Dockerfile can be used for building Windows Server 2019, 2022 Container images.
+
+# Build Container image from msi installer
+ARG IMAGE_TAG=ltsc2022
+ARG BUILD_IMAGE=mcr.microsoft.com/windows/servercore:$IMAGE_TAG
+ARG TARGETARCH=amd64
+ARG CONTAINER_CLOUDWATCHAGENT_PATH=C:\\Program\ Files\\Amazon\\AmazonCloudWatchAgent\\
+
+FROM $BUILD_IMAGE
+
+ARG TARGETARCH
+ARG CONTAINER_CLOUDWATCHAGENT_PATH
+
+COPY ${TARGETARCH}/amazon-cloudwatch-agent.msi C:\\tmp\\amazon-cloudwatch-agent.msi
+RUN msiexec /i C:\\tmp\\amazon-cloudwatch-agent.msi
+
+WORKDIR $CONTAINER_CLOUDWATCHAGENT_PATH
+
+ENV RUN_IN_CONTAINER="True"
+CMD ["start-amazon-cloudwatch-agent.exe"]
diff --git a/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/source/Dockerfile.Windows b/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/source/Dockerfile.Windows
new file mode 100644
index 0000000000..507df88de4
--- /dev/null
+++ b/amazon-cloudwatch-container-insights/cloudwatch-agent-dockerfile/source/Dockerfile.Windows
@@ -0,0 +1,45 @@
+# This Dockerfile can be used for building Windows Server 2019, 2022 Container images.
+
+ARG TAG=ltsc2022
+ARG TARGETARCH=amd64
+ARG CONTAINER_CLOUDWATCHAGENT_PATH=C:\\Program\ Files\\Amazon\\AmazonCloudWatchAgent\\
+ARG GO_IMAGE=golang:latest
+
+# Build CW agent inside Windows golang container
+FROM $GO_IMAGE as builder
+
+ARG TARGETARCH
+
+RUN New-Item -ItemType Directory -Path "C:\go\src\github.com\aws\amazon-cloudwatch-agent" -Force
+WORKDIR "C:\go\src\github.com\aws\amazon-cloudwatch-agent"
+
+ENV GOPROXY=direct
+ARG GO111MODULE="on"
+ENV GO111MODULE=${GO111MODULE}
+
+COPY go.mod "C:\go\src\github.com\aws\amazon-cloudwatch-agent"
+COPY go.sum "C:\go\src\github.com\aws\amazon-cloudwatch-agent"
+RUN go mod download -x
+
+COPY . "C:\go\src\github.com\aws\amazon-cloudwatch-agent"
+
+# Install chocolatey and make
+RUN Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))
+RUN choco install make
+
+# Run make and build CW agent inside container
+RUN make build-for-docker-windows-${env:TARGETARCH}
+
+# Build target CW agent container image for Windows
+FROM mcr.microsoft.com/windows/servercore:$TAG
+
+ARG CONTAINER_CLOUDWATCHAGENT_PATH
+ARG TARGETARCH
+
+RUN Powershell -Command New-Item -ItemType Directory -Path $env:CONTAINER_CLOUDWATCHAGENT_PATH -Force
+WORKDIR $CONTAINER_CLOUDWATCHAGENT_PATH
+
+COPY --from=builder C:\\go\\src\\github.com\\aws\\amazon-cloudwatch-agent\\build\\bin\\windows_$TARGETARCH\\ $CONTAINER_CLOUDWATCHAGENT_PATH
+
+ENV RUN_IN_CONTAINER="True"
+CMD ["start-amazon-cloudwatch-agent.exe"]
\ No newline at end of file
diff --git a/cfg/envconfig/envconfig.go b/cfg/envconfig/envconfig.go
index 67e85a8021..a0cd44327c 100644
--- a/cfg/envconfig/envconfig.go
+++ b/cfg/envconfig/envconfig.go
@@ -5,29 +5,31 @@ package envconfig
 
 import (
 	"os"
+	"runtime"
 	"strconv"
 	"sync"
 )
 
 const (
 	//the following are the names of environment variables
-	HTTP_PROXY         = "HTTP_PROXY"
-	HTTPS_PROXY        = "HTTPS_PROXY"
-	NO_PROXY           = "NO_PROXY"
-	AWS_CA_BUNDLE      = "AWS_CA_BUNDLE"
-	AWS_SDK_LOG_LEVEL  = "AWS_SDK_LOG_LEVEL"
-	CWAGENT_USER_AGENT = "CWAGENT_USER_AGENT"
-	CWAGENT_LOG_LEVEL  = "CWAGENT_LOG_LEVEL"
-	CWAGENT_USAGE_DATA = "CWAGENT_USAGE_DATA"
-	IMDS_NUMBER_RETRY  = "IMDS_NUMBER_RETRY"
-	RunInContainer     = "RUN_IN_CONTAINER"
-	RunInAWS           = "RUN_IN_AWS"
-	RunWithIRSA        = "RUN_WITH_IRSA"
-	UseDefaultConfig   = "USE_DEFAULT_CONFIG"
-	HostName           = "HOST_NAME"
-	PodName            = "POD_NAME"
-	HostIP             = "HOST_IP"
-	CWConfigContent    = "CW_CONFIG_CONTENT"
+	HTTP_PROXY                = "HTTP_PROXY"
+	HTTPS_PROXY               = "HTTPS_PROXY"
+	NO_PROXY                  = "NO_PROXY"
+	AWS_CA_BUNDLE             = "AWS_CA_BUNDLE"
+	AWS_SDK_LOG_LEVEL         = "AWS_SDK_LOG_LEVEL"
+	CWAGENT_USER_AGENT        = "CWAGENT_USER_AGENT"
+	CWAGENT_LOG_LEVEL         = "CWAGENT_LOG_LEVEL"
+	CWAGENT_USAGE_DATA        = "CWAGENT_USAGE_DATA"
+	IMDS_NUMBER_RETRY         = "IMDS_NUMBER_RETRY"
+	RunInContainer            = "RUN_IN_CONTAINER"
+	RunAsHostProcessContainer = "RUN_AS_HOST_PROCESS_CONTAINER"
+	RunInAWS                  = "RUN_IN_AWS"
+	RunWithIRSA               = "RUN_WITH_IRSA"
+	UseDefaultConfig          = "USE_DEFAULT_CONFIG"
+	HostName                  = "HOST_NAME"
+	PodName                   = "POD_NAME"
+	HostIP                    = "HOST_IP"
+	CWConfigContent           = "CW_CONFIG_CONTENT"
 )
 
 const (
@@ -57,3 +59,10 @@ func IsUsageDataEnabled() bool {
 func IsRunningInContainer() bool {
 	return os.Getenv(RunInContainer) == TrueValue
 }
+
+func IsWindowsHostProcessContainer() bool {
+	if runtime.GOOS == "windows" && os.Getenv(RunInContainer) == TrueValue && os.Getenv(RunAsHostProcessContainer) == TrueValue {
+		return true
+	}
+	return false
+}
diff --git a/cmd/start-amazon-cloudwatch-agent/path_windows.go b/cmd/start-amazon-cloudwatch-agent/path_windows.go
index 19c01a2ef7..8337a6f0ee 100644
--- a/cmd/start-amazon-cloudwatch-agent/path_windows.go
+++ b/cmd/start-amazon-cloudwatch-agent/path_windows.go
@@ -10,25 +10,44 @@ import (
 	"fmt"
 	"io"
 	"log"
+	"os"
 	"os/exec"
 
 	"github.com/aws/amazon-cloudwatch-agent/tool/paths"
+	"github.com/aws/amazon-cloudwatch-agent/translator/config"
 )
 
 func startAgent(writer io.WriteCloser) error {
-	if err := writer.Close(); err != nil {
-		log.Printf("E! Cannot close the log file, ERROR is %v \n", err)
+
+	if os.Getenv(config.RUN_IN_CONTAINER) != config.RUN_IN_CONTAINER_TRUE {
+		if err := writer.Close(); err != nil {
+			log.Printf("E! Cannot close the log file, ERROR is %v \n", err)
+			return err
+		}
+		cmd := exec.Command(
+			paths.AgentBinaryPath,
+			"-config", paths.TomlConfigPath,
+			"-envconfig", paths.EnvConfigPath,
+			"-otelconfig", paths.YamlConfigPath,
+		)
+		stdoutStderr, err := cmd.CombinedOutput()
+		// log file is closed, so use fmt here
+		fmt.Printf("%s \n", stdoutStderr)
+		return err
+	} else {
+		cmd := exec.Command(
+			paths.AgentBinaryPath,
+			"-config", paths.TomlConfigPath,
+			"-envconfig", paths.EnvConfigPath,
+			"-otelconfig", paths.YamlConfigPath,
+			"-console", "true",
+		)
+		cmd.Stdin = os.Stdin
+		cmd.Stdout = os.Stdout
+		cmd.Stderr = os.Stderr
+		err := cmd.Run()
+		fmt.Printf("%s \n", err)
 		return err
 	}
 
-	cmd := exec.Command(
-		paths.AgentBinaryPath,
-		"-config", paths.TomlConfigPath,
-		"-envconfig", paths.EnvConfigPath,
-		"-otelconfig", paths.YamlConfigPath,
-	)
-	stdoutStderr, err := cmd.CombinedOutput()
-	// log file is closed, so use fmt here
-	fmt.Printf("%s \n", stdoutStderr)
-	return err
 }
diff --git a/go.mod b/go.mod
index 8beac47726..8b9a47ef42 100644
--- a/go.mod
+++ b/go.mod
@@ -7,38 +7,39 @@ replace github.com/influxdata/telegraf => github.com/aws/telegraf v0.10.2-0.2023
 // Replace with https://github.com/amazon-contributing/opentelemetry-collector-contrib, there are no requirements for all receivers/processors/exporters
 // to be all replaced since there are some changes that will always be from upstream
 replace (
-	github.com/open-telemetry/opentelemetry-collector-contrib/exporter/awscloudwatchlogsexporter => github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awscloudwatchlogsexporter v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/exporter/awsemfexporter => github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awsemfexporter v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/exporter/awsxrayexporter => github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awsxrayexporter v0.0.0-20240301221517-9cb314e7d27b
+	github.com/open-telemetry/opentelemetry-collector-contrib/exporter/awscloudwatchlogsexporter => github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awscloudwatchlogsexporter v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/exporter/awsemfexporter => github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awsemfexporter v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/exporter/awsxrayexporter => github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awsxrayexporter v0.0.0-20240307151043-a7e0c68e9895
 )
 
-replace github.com/open-telemetry/opentelemetry-collector-contrib/extension/awsproxy => github.com/amazon-contributing/opentelemetry-collector-contrib/extension/awsproxy v0.0.0-20240301221517-9cb314e7d27b
+replace github.com/open-telemetry/opentelemetry-collector-contrib/extension/awsproxy => github.com/amazon-contributing/opentelemetry-collector-contrib/extension/awsproxy v0.0.0-20240307151043-a7e0c68e9895
 
 replace (
-	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/awsutil => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/awsutil v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/containerinsight => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/containerinsight v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/cwlogs => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/cwlogs v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/k8s => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/k8s v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/proxy => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/proxy v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/xray => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/xray v0.0.0-20240301221517-9cb314e7d27b
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/awsutil => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/awsutil v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/containerinsight => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/containerinsight v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/cwlogs => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/cwlogs v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/k8s => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/k8s v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/proxy => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/proxy v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/aws/xray => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/aws/xray v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/internal/kubelet => github.com/amazon-contributing/opentelemetry-collector-contrib/internal/kubelet v0.0.0-20240307151043-a7e0c68e9895
 )
 
 replace (
-	github.com/open-telemetry/opentelemetry-collector-contrib/pkg/stanza => github.com/amazon-contributing/opentelemetry-collector-contrib/pkg/stanza v0.0.0-20240301221517-9cb314e7d27b
+	github.com/open-telemetry/opentelemetry-collector-contrib/pkg/stanza => github.com/amazon-contributing/opentelemetry-collector-contrib/pkg/stanza v0.0.0-20240307151043-a7e0c68e9895
 	// Replace with contrib to revert upstream change https://github.com/open-telemetry/opentelemetry-collector-contrib/pull/20519
-	github.com/open-telemetry/opentelemetry-collector-contrib/pkg/translator/prometheus => github.com/amazon-contributing/opentelemetry-collector-contrib/pkg/translator/prometheus v0.0.0-20240301221517-9cb314e7d27b
+	github.com/open-telemetry/opentelemetry-collector-contrib/pkg/translator/prometheus => github.com/amazon-contributing/opentelemetry-collector-contrib/pkg/translator/prometheus v0.0.0-20240307151043-a7e0c68e9895
 )
 
-replace github.com/open-telemetry/opentelemetry-collector-contrib/processor/resourcedetectionprocessor => github.com/amazon-contributing/opentelemetry-collector-contrib/processor/resourcedetectionprocessor v0.0.0-20240301221517-9cb314e7d27b
+replace github.com/open-telemetry/opentelemetry-collector-contrib/processor/resourcedetectionprocessor => github.com/amazon-contributing/opentelemetry-collector-contrib/processor/resourcedetectionprocessor v0.0.0-20240307151043-a7e0c68e9895
 
 replace (
-	github.com/open-telemetry/opentelemetry-collector-contrib/receiver/awscontainerinsightreceiver => github.com/amazon-contributing/opentelemetry-collector-contrib/receiver/awscontainerinsightreceiver v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/receiver/awsxrayreceiver => github.com/amazon-contributing/opentelemetry-collector-contrib/receiver/awsxrayreceiver v0.0.0-20240301221517-9cb314e7d27b
-	github.com/open-telemetry/opentelemetry-collector-contrib/receiver/prometheusreceiver => github.com/amazon-contributing/opentelemetry-collector-contrib/receiver/prometheusreceiver v0.0.0-20240301221517-9cb314e7d27b
+	github.com/open-telemetry/opentelemetry-collector-contrib/receiver/awscontainerinsightreceiver => github.com/amazon-contributing/opentelemetry-collector-contrib/receiver/awscontainerinsightreceiver v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/receiver/awsxrayreceiver => github.com/amazon-contributing/opentelemetry-collector-contrib/receiver/awsxrayreceiver v0.0.0-20240307151043-a7e0c68e9895
+	github.com/open-telemetry/opentelemetry-collector-contrib/receiver/prometheusreceiver => github.com/amazon-contributing/opentelemetry-collector-contrib/receiver/prometheusreceiver v0.0.0-20240307151043-a7e0c68e9895
 )
 
 // Omit fields in HTTPClientSettings. Pending fix for https://github.com/open-telemetry/opentelemetry-collector/issues/8627
-replace go.opentelemetry.io/collector/config/confighttp => github.com/amazon-contributing/opentelemetry-collector-contrib/config/confighttp v0.0.0-20240301221517-9cb314e7d27b
+replace go.opentelemetry.io/collector/config/confighttp => github.com/amazon-contributing/opentelemetry-collector-contrib/config/confighttp v0.0.0-20240307151043-a7e0c68e9895
 
 // Temporary fix, pending PR https://github.com/shirou/gopsutil/pull/957
 replace github.com/shirou/gopsutil/v3 => github.com/aws/telegraf/patches/gopsutil/v3 v3.0.0-20231109213610-a8c21c54a2be // indirect
@@ -184,6 +185,7 @@ require (
 	github.com/Azure/go-autorest/tracing v0.6.0 // indirect
 	github.com/GoogleCloudPlatform/opentelemetry-operations-go/detectors/gcp v1.20.0 // indirect
 	github.com/Microsoft/go-winio v0.6.1 // indirect
+	github.com/Microsoft/hcsshim v0.11.4 // indirect
 	github.com/Showmax/go-fqdn v1.0.0 // indirect
 	github.com/alecthomas/participle v0.4.1 // indirect
 	github.com/alecthomas/participle/v2 v2.1.0 // indirect
@@ -211,7 +213,9 @@ require (
 	github.com/checkpoint-restore/go-criu/v5 v5.3.0 // indirect
 	github.com/cilium/ebpf v0.9.1 // indirect
 	github.com/cncf/xds/go v0.0.0-20230607035331-e9ce68804cb4 // indirect
+	github.com/containerd/cgroups v1.1.0 // indirect
 	github.com/containerd/console v1.0.3 // indirect
+	github.com/containerd/containerd v1.7.7 // indirect
 	github.com/containerd/ttrpc v1.2.2 // indirect
 	github.com/coreos/go-semver v0.3.0 // indirect
 	github.com/coreos/go-systemd/v22 v22.5.0 // indirect
@@ -421,6 +425,7 @@ require (
 	gopkg.in/yaml.v2 v2.4.0 // indirect
 	k8s.io/klog v1.0.0 // indirect
 	k8s.io/kube-openapi v0.0.0-20230717233707-2695361300d9 // indirect
+	k8s.io/kubelet v0.28.3 // indirect
 	k8s.io/utils v0.0.0-20230711102312-30195339c3c7 // indirect
 	sigs.k8s.io/json v0.0.0-20221116044647-bc3834ca7abd // indirect
 	sigs.k8s.io/structured-merge-diff/v4 v4.3.0 // indirect
diff --git a/go.sum b/go.sum
index e104a0946c..ad1dec8e29 100644
--- a/go.sum
+++ b/go.sum
@@ -103,6 +103,8 @@ github.com/Knetic/govaluate v3.0.1-0.20171022003610-9aa49832a739+incompatible/go
 github.com/Mellanox/rdmamap v0.0.0-20191106181932-7c3c4763a6ee h1:atI/FFjXh6hIVlPE1Jup9m8N4B9q/OSbMUe2EBahs+w=
 github.com/Microsoft/go-winio v0.6.1 h1:9/kr64B9VUZrLm5YYwbGtUJnMgqWVOdUAXu6Migciow=
 github.com/Microsoft/go-winio v0.6.1/go.mod h1:LRdKpFKfdobln8UmuiYcKPot9D2v6svN5+sAH+4kjUM=
+github.com/Microsoft/hcsshim v0.11.4 h1:68vKo2VN8DE9AdN4tnkWnmdhqdbpUFM8OF3Airm7fz8=
+github.com/Microsoft/hcsshim v0.11.4/go.mod h1:smjE4dvqPX9Zldna+t5FG3rnoHhaB7QYxPRqGcpAD9w=
 github.com/NYTimes/gziphandler v0.0.0-20170623195520-56545f4a5d46/go.mod h1:3wb06e3pkSAbeQ52E9H9iFoQsEEwGN64994WTCIhntQ=
 github.com/OneOfOne/xxhash v1.2.2/go.mod h1:HSdplMjZKSmBqAxg5vPj2TmRDmfkzw+cTzAElWljhcU=
 github.com/PuerkitoBio/purell v1.1.1/go.mod h1:c11w/QuzBsJSee3cPx9rAFu61PvFxuPbtSwDGJws/X0=
@@ -134,44 +136,46 @@ github.com/alecthomas/units v0.0.0-20190924025748-f65c72e2690d/go.mod h1:rBZYJk5
 github.com/alecthomas/units v0.0.0-20211218093645-b94a6e3cc137 h1:s6gZFSlWYmbqAuRjVTiNNhvNRfY2Wxp9nhfyel4rklc=
 github.com/alecthomas/units v0.0.0-20211218093645-b94a6e3cc137/go.mod h1:OMCwj8VM1Kc9e19TLln2VL61YJF0x1XFtfdL4JdbSyE=
 github.com/aliyun/alibaba-cloud-sdk-go v1.61.1483 h1:J8HaD+Zpfi1gcel3HCKpoHHEsrcuRrZlSnx7R9SCf5I=
-github.com/amazon-contributing/opentelemetry-collector-contrib/config/confighttp v0.0.0-20240301221517-9cb314e7d27b h1:JbyxYa3c8PQRpQZpEekKvWMTk2iSiT/M79WikF7vQQQ=
-github.com/amazon-contributing/opentelemetry-collector-contrib/config/confighttp v0.0.0-20240301221517-9cb314e7d27b/go.mod h1:3sU3HgF5wc32CVljnzGo4Fn/9+T0N1Z6tCJyKdW2MvM=
-github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awscloudwatchlogsexporter v0.0.0-20240301221517-9cb314e7d27b h1:ejIXrN48i5YDshcb+Kwy5IPgwfHvkUXMfdxzjbvVOMU=
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-github.com/amazon-contributing/opentelemetry-collector-contrib/exporter/awsemfexporter v0.0.0-20240301221517-9cb314e7d27b h1:82/jRNSmc+EzC63bGqfjFDSsQjPWU8OwxoJd9jpIJqI=
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 github.com/amir/raidman v0.0.0-20170415203553-1ccc43bfb9c9 h1:FXrPTd8Rdlc94dKccl7KPmdmIbVh/OjelJ8/vgMRzcQ=
 github.com/andybalholm/brotli v1.0.4 h1:V7DdXeJtZscaqfNuAdSRuRFzuiKlHSC/Zh3zl9qY3JY=
 github.com/antchfx/jsonquery v1.1.5 h1:1YWrNFYCcIuJPIjFeOP5b6TXbLSUYY8qqxWbuZOB1qE=
@@ -293,8 +297,12 @@ github.com/cncf/udpa/go v0.0.0-20201120205902-5459f2c99403/go.mod h1:WmhPx2Nbnht
 github.com/cncf/xds/go v0.0.0-20210312221358-fbca930ec8ed/go.mod h1:eXthEFrGJvWHgFFCl3hGmgk+/aYT6PnTQLykKQRLhEs=
 github.com/cncf/xds/go v0.0.0-20230607035331-e9ce68804cb4 h1:/inchEIKaYC1Akx+H+gqO04wryn5h75LSazbRlnya1k=
 github.com/cncf/xds/go v0.0.0-20230607035331-e9ce68804cb4/go.mod h1:eXthEFrGJvWHgFFCl3hGmgk+/aYT6PnTQLykKQRLhEs=
+github.com/containerd/cgroups v1.1.0 h1:v8rEWFl6EoqHB+swVNjVoCJE8o3jX7e8nqBGPLaDFBM=
+github.com/containerd/cgroups v1.1.0/go.mod h1:6ppBcbh/NOOUU+dMKrykgaBnK9lCIBxHqJDGwsa1mIw=
 github.com/containerd/console v1.0.3 h1:lIr7SlA5PxZyMV30bDW0MGbiOPXwc63yRuCP0ARubLw=
 github.com/containerd/console v1.0.3/go.mod h1:7LqA/THxQ86k76b8c/EMSiaJ3h1eZkMkXar0TQ1gf3U=
+github.com/containerd/containerd v1.7.7 h1:QOC2K4A42RQpcrZyptP6z9EJZnlHfHJUfZrAAHe15q4=
+github.com/containerd/containerd v1.7.7/go.mod h1:3c4XZv6VeT9qgf9GMTxNTMFxGJrGpI2vz1yk4ye+YY8=
 github.com/containerd/ttrpc v1.2.2 h1:9vqZr0pxwOF5koz6N0N3kJ0zDHokrcPxIR/ZR2YFtOs=
 github.com/containerd/ttrpc v1.2.2/go.mod h1:sIT6l32Ph/H9cvnJsfXM5drIVzTr5A2flTf1G5tYZak=
 github.com/containerd/typeurl v1.0.2 h1:Chlt8zIieDbzQFzXzAeBEF92KhExuE4p9p92/QmY7aY=
@@ -922,8 +930,6 @@ github.com/open-telemetry/opentelemetry-collector-contrib/internal/filter v0.89.
 github.com/open-telemetry/opentelemetry-collector-contrib/internal/filter v0.89.0/go.mod h1:/fuCFCuI8B9ViltKiw2xZEKdTEcEZMbPAajRfJqF9mg=
 github.com/open-telemetry/opentelemetry-collector-contrib/internal/k8sconfig v0.89.0 h1:LP0znKNQsJHqWVRKTzZcgnJEQv4730XBe1tzTFkVHQE=
 github.com/open-telemetry/opentelemetry-collector-contrib/internal/k8sconfig v0.89.0/go.mod h1:1mxlOOYVp1/QGKM13X1m1ZUJa0GJ2Lvz/URC9d8FC1s=
-github.com/open-telemetry/opentelemetry-collector-contrib/internal/kubelet v0.89.0 h1:bWeWdtqT+GryeILIJ64eChhgkVoj4Ireczxr9C1hWKg=
-github.com/open-telemetry/opentelemetry-collector-contrib/internal/kubelet v0.89.0/go.mod h1:JszEiY5P2i7sL6LAsic+TM/C3FWHRL0wbazfVmIdPE0=
 github.com/open-telemetry/opentelemetry-collector-contrib/internal/metadataproviders v0.89.0 h1:NElphJJuMTt/LBFULiN4IuMWKwNWBxb+SgWBWE7V4BU=
 github.com/open-telemetry/opentelemetry-collector-contrib/internal/metadataproviders v0.89.0/go.mod h1:B13GrpB/gdZKCOk1e40uIDefGxZI7745nxhBZ28MwAw=
 github.com/open-telemetry/opentelemetry-collector-contrib/pkg/golden v0.89.0 h1:GAI5zG4W6wo20qVLvZjamskPYh7JEPEPMboElWxWzQE=
@@ -1802,6 +1808,8 @@ k8s.io/klog/v2 v2.100.1/go.mod h1:y1WjHnz7Dj687irZUWR/WLkLc5N1YHtjLdmgWjndZn0=
 k8s.io/kube-openapi v0.0.0-20210305001622-591a79e4bda7/go.mod h1:wXW5VT87nVfh/iLV8FpR2uDvrFyomxbtb1KivDbvPTE=
 k8s.io/kube-openapi v0.0.0-20230717233707-2695361300d9 h1:LyMgNKD2P8Wn1iAwQU5OhxCKlKJy0sHc+PcDwFB24dQ=
 k8s.io/kube-openapi v0.0.0-20230717233707-2695361300d9/go.mod h1:wZK2AVp1uHCp4VamDVgBP2COHZjqD1T68Rf0CM3YjSM=
+k8s.io/kubelet v0.28.3 h1:bp/uIf1R5F61BlFvFtzc4PDEiK7TtFcw3wFJlc0V0LM=
+k8s.io/kubelet v0.28.3/go.mod h1:E3NHYbp/v45Ao6AD0EOZnqO3L0R6Haks6Nm0+bnFwtU=
 k8s.io/utils v0.0.0-20201110183641-67b214c5f920/go.mod h1:jPW/WVKK9YHAvNhRxK0md/EJ228hCsBRufyofKtW8HA=
 k8s.io/utils v0.0.0-20230711102312-30195339c3c7 h1:ZgnF1KZsYxWIifwSNZFZgNtWE89WI5yiP5WwlfDoIyc=
 k8s.io/utils v0.0.0-20230711102312-30195339c3c7/go.mod h1:OLgZIPagt7ERELqWJFomSt595RzquPNLL48iOWgYOg0=
diff --git a/tool/paths/paths.go b/tool/paths/paths.go
index 26543934fb..dc612bdf39 100644
--- a/tool/paths/paths.go
+++ b/tool/paths/paths.go
@@ -10,8 +10,6 @@ const (
 	YAML           = "amazon-cloudwatch-agent.yaml"
 	ENV            = "env-config.json"
 	AGENT_LOG_FILE = "amazon-cloudwatch-agent.log"
-	//TODO this CONFIG_DIR_IN_CONTAINER should change to something indicate dir, keep it for now to avoid break testing
-	CONFIG_DIR_IN_CONTAINER = "/etc/cwagentconfig"
 )
 
 var (
diff --git a/tool/paths/paths_unix.go b/tool/paths/paths_unix.go
index c59c70232a..a99a39a4a9 100644
--- a/tool/paths/paths_unix.go
+++ b/tool/paths/paths_unix.go
@@ -16,6 +16,8 @@ const (
 	AgentBinaryName      = "amazon-cloudwatch-agent"
 	WizardBinaryName     = "amazon-cloudwatch-agent-config-wizard"
 	AgentStartName       = "amazon-cloudwatch-agent-ctl"
+	//TODO this CONFIG_DIR_IN_CONTAINER should change to something indicate dir, keep it for now to avoid break testing
+	CONFIG_DIR_IN_CONTAINER = "/etc/cwagentconfig"
 )
 
 func init() {
diff --git a/tool/paths/paths_windows.go b/tool/paths/paths_windows.go
index 69c51ac889..2d8eca162b 100644
--- a/tool/paths/paths_windows.go
+++ b/tool/paths/paths_windows.go
@@ -9,6 +9,8 @@ package paths
 import (
 	"os"
 	"path/filepath"
+
+	"github.com/aws/amazon-cloudwatch-agent/cfg/envconfig"
 )
 
 const (
@@ -21,6 +23,8 @@ const (
 	AgentStartName       = "amazon-cloudwatch-agent-ctl.ps1"
 )
 
+var CONFIG_DIR_IN_CONTAINER = filepath.Join(os.Getenv("ProgramFiles"), AgentDir, "cwagentconfig")
+
 func init() {
 	programFiles := os.Getenv("ProgramFiles")
 	var programData string
@@ -31,6 +35,12 @@ func init() {
 		programData = filepath.Join(os.Getenv("ALLUSERSPROFILE"), "Application Data")
 	}
 
+	if envconfig.IsWindowsHostProcessContainer() {
+		CONFIG_DIR_IN_CONTAINER = filepath.Join(os.Getenv("CONTAINER_SANDBOX_MOUNT_POINT"), "Program Files", AgentDir, "cwagentconfig", "cwagentconfig.json")
+		programFiles = filepath.Join(os.Getenv("CONTAINER_SANDBOX_MOUNT_POINT"), "Program Files")
+		programData = filepath.Join(os.Getenv("CONTAINER_SANDBOX_MOUNT_POINT"), "ProgramData")
+	}
+
 	AgentRootDir := filepath.Join(programFiles, AgentDir)
 	AgentConfigDir := filepath.Join(programData, AgentDir)
 	JsonConfigPath = filepath.Join(AgentConfigDir, JSON)
diff --git a/translator/cmdutil/translatorutil.go b/translator/cmdutil/translatorutil.go
index 70f54e4499..c2f7357287 100644
--- a/translator/cmdutil/translatorutil.go
+++ b/translator/cmdutil/translatorutil.go
@@ -13,6 +13,7 @@ import (
 	"github.com/xeipuuv/gojsonschema"
 	"go.opentelemetry.io/collector/confmap"
 
+	"github.com/aws/amazon-cloudwatch-agent/cfg/envconfig"
 	"github.com/aws/amazon-cloudwatch-agent/translator"
 	"github.com/aws/amazon-cloudwatch-agent/translator/config"
 	"github.com/aws/amazon-cloudwatch-agent/translator/context"
@@ -129,21 +130,26 @@ func GenerateMergedJsonConfigMap(ctx *context.Context) (map[string]interface{},
 				fmt.Printf("Cannot access %v: %v \n", path, err)
 				return err
 			}
-			if info.Mode()&os.ModeSymlink != 0 {
-				log.Printf("Find symbolic link %s \n", path)
-				path, err := filepath.EvalSymlinks(path)
-				if err != nil {
-					log.Printf("Symbolic link %v will be ignored due to err: %v. \n", path, err)
-					return nil
+			if envconfig.IsWindowsHostProcessContainer() {
+				log.Printf("Skipping checking symbolic link for Windows host process containers %s. \n"+
+					"These symbolic links are skipped as valuating symlinks is common failures for Windows containers", path)
+			} else {
+				if info.Mode()&os.ModeSymlink != 0 {
+					log.Printf("Find symbolic link %s \n", path)
+					path, err := filepath.EvalSymlinks(path)
+					if err != nil {
+						log.Printf("Symbolic link %v will be ignored due to err: %v. \n", path, err)
+						return nil
+					}
+					info, err = os.Stat(path)
+					if err != nil {
+						log.Printf("Path %v will be ignored due to err: %v. \n", path, err)
+					}
 				}
-				info, err = os.Stat(path)
-				if err != nil {
-					log.Printf("Path %v will be ignored due to err: %v. \n", path, err)
+				if info.IsDir() {
+					return nil
 				}
 			}
-			if info.IsDir() {
-				return nil
-			}
 
 			if filepath.Ext(path) == context.TmpFileSuffix {
 				// .tmp files