diff --git a/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec b/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec
index bb797448364..70ee7484a1f 100644
--- a/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec
+++ b/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec
@@ -4,7 +4,7 @@
   <metadata>
     <id>asyncapi</id>
     <version>{{version}}</version>
-    <packageSourceUrl>https://github.com/asyncapi/cli/releases</packageSourceUrl>
+    <packageSourceUrl>https://github.com/asyncapi/cli/releases/v{{version}}</packageSourceUrl>
     <owners>AsyncAPI_Initiative</owners>
 
     <!-- == SOFTWARE SPECIFIC SECTION == -->
diff --git a/.github/workflows/deploy/chocolatey/replace.ps1 b/.github/workflows/deploy/chocolatey/replace.ps1
index fcacc27eac8..c92cc866bda 100644
--- a/.github/workflows/deploy/chocolatey/replace.ps1
+++ b/.github/workflows/deploy/chocolatey/replace.ps1
@@ -1,6 +1,8 @@
 param (
   [Parameter(Mandatory=$true)]
-  [string]$version
+  [string]$version,
+  [string]$checksum,
+  [string]$checksum64
 )
 
 $filePaths = @(
@@ -11,5 +13,7 @@ $filePaths = @(
 foreach ($filePath in $filePaths) {
   $fileContents = Get-Content $filePath
   $fileContents = $fileContents -replace '{{version}}', $version
+  $fileContents = $fileContents -replace '{{checksum}}', $checksum
+  $fileContents = $fileContents -replace '{{checksum64}}', $checksum64
   Set-Content $filePath $fileContents
 }
\ No newline at end of file
diff --git a/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1 b/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1
index 5851aa3ba16..51049d73182 100644
--- a/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1
+++ b/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1
@@ -14,11 +14,10 @@ $packageArgs = @{
 
   softwareName  = 'asyncapi-cli*'
 
-  # TODO :- Change the checksum and checksumType to match the checksums for the above file.
-  # checksum      = ''
-  # checksumType  = 'sha256' #default is md5, can also be sha1, sha256 or sha512
-  # checksum64    = ''
-  # checksumType64= 'sha256' #default is checksumType
+  checksum      = '{{checksum}}'
+  checksumType  = 'sha256' #default is md5, can also be sha1, sha256 or sha512
+  checksum64    = '{{checksum64}}'
+  checksumType64= 'sha256' #default is checksumType
 
   validExitCodes= @(0, 3010, 1641)
   silentArgs   = '/S'           # NSIS
diff --git a/.github/workflows/release-chocolatey.yml b/.github/workflows/release-chocolatey.yml
index b660240565c..8aef0996e4c 100644
--- a/.github/workflows/release-chocolatey.yml
+++ b/.github/workflows/release-chocolatey.yml
@@ -18,6 +18,7 @@ jobs:
     steps:
       - name: Checkout
         uses: actions/checkout@v3
+
       - name: Set Version
         id: release_version
         run: |
@@ -29,16 +30,36 @@ jobs:
           }
           echo "Setting version to $version"
           echo "version=$version" >> $env:GITHUB_OUTPUT
+
+      - name: Download release
+        run: |
+          echo "Downloading release assets for version ${{ steps.release_version.outputs.version }}"
+          mkdir -p ./dist/win32
+          curl -L "https://github.com/asyncapi/cli/releases/download/v${{ steps.release_version.outputs.version }}/asyncapi.x64.exe" -o "./dist/win32/asyncapi.x64.exe"
+          curl -L "https://github.com/asyncapi/cli/releases/download/v${{ steps.release_version.outputs.version }}/asyncapi.x86.exe" -o "./dist/win32/asyncapi.x86.exe"
+
+      - name: Get Checksum of the release
+        id: release_checksum
+        run: |
+          $checksum = (Get-FileHash -Path "./dist/win32/asyncapi.x86.exe" -Algorithm SHA256).Hash
+          $checksum64 = (Get-FileHash -Path "./dist/win32/asyncapi.x64.exe" -Algorithm SHA256).Hash
+          echo "Setting checksum to $checksum"
+          echo "checksum=$checksum" >> $env:GITHUB_OUTPUT
+          echo "Setting checksum64 to $checksum64"
+          echo "checksum64=$checksum64" >> $env:GITHUB_OUTPUT
+
       - name: Make nuspec from the template
         run: |
           cd ./.github/workflows/deploy/chocolatey
-          pwsh -File ./replace.ps1 -version ${{ steps.release_version.outputs.version }}
+          pwsh -File ./replace.ps1 -version ${{ steps.release_version.outputs.version }} -checksum ${{ steps.release_checksum.outputs.checksum }} -checksum64 ${{ steps.release_checksum.outputs.checksum64 }}
+
       - name: Run Chocolatey Pack
         run: |
           cd ./.github/workflows/deploy/chocolatey
           choco pack ./asyncapi-cli.nuspec
           choco apikey add --source "'https://push.chocolatey.org/'" --key ${{ secrets.CHOCOLATEY_API_KEY }}
           choco push ./asyncapi.${{ steps.release_version.outputs.version }}.nupkg --source "'https://push.chocolatey.org/'"  
+          
       - if: failure() # Only, on failure, send a message on the 94_bot-failing-ci slack channel
         name: Report workflow run status to Slack
         uses: 8398a7/action-slack@fbd6aa58ba854a740e11a35d0df80cb5d12101d8 #using https://github.com/8398a7/action-slack/releases/tag/v3.15.1