diff --git a/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec b/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec
new file mode 100644
index 00000000000..f15e171f812
--- /dev/null
+++ b/.github/workflows/deploy/chocolatey/asyncapi-cli.nuspec
@@ -0,0 +1,29 @@
+<?xml version="1.0" encoding="utf-8"?>
+<!-- Do not remove this test for UTF-8: if “Ω” doesn’t appear as greek uppercase omega letter enclosed in quotation marks, you should use an editor that supports UTF-8, not this one. -->
+<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
+  <metadata>
+    <id>asyncapi</id>
+    <version>{{version}}</version>
+    <packageSourceUrl>https://github.com/asyncapi/cli/releases</packageSourceUrl>
+    <owners>AsyncAPI, shurtugal</owners>
+
+    <!-- == SOFTWARE SPECIFIC SECTION == -->
+    <!-- This section is about the software itself -->
+    <title>asyncapi-cli</title>
+    <authors>AsyncAPI, shurtugal</authors>
+    <projectUrl>https://www.asyncapi.com/</projectUrl>
+    <iconUrl>https://avatars.githubusercontent.com/u/16401334?s=200</iconUrl>
+    <copyright>2023 AsyncAPI</copyright>
+    <licenseUrl>https://github.com/asyncapi/cli/blob/master/LICENSE</licenseUrl>
+    <requireLicenseAcceptance>false</requireLicenseAcceptance>
+    <projectSourceUrl>https://github.com/asyncapi/cli</projectSourceUrl>
+    <docsUrl>https://www.asyncapi.com/docs/tools/cli</docsUrl>
+    <bugTrackerUrl>https://github.com/asyncapi/cli/issues/new/choose</bugTrackerUrl>
+    <tags>asyncapi-cli cli nodejs api asyncapi</tags>
+    <description>CLI to work with your AsyncAPI files. You can validate them and in the future use a generator and even bootstrap a new file. Contributions are welcomed!</description>
+  </metadata>
+  <files>
+    <!-- this section controls what actually gets packaged into the Chocolatey package -->
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/.github/workflows/deploy/chocolatey/replace.ps1 b/.github/workflows/deploy/chocolatey/replace.ps1
new file mode 100644
index 00000000000..fcacc27eac8
--- /dev/null
+++ b/.github/workflows/deploy/chocolatey/replace.ps1
@@ -0,0 +1,15 @@
+param (
+  [Parameter(Mandatory=$true)]
+  [string]$version
+)
+
+$filePaths = @(
+  './tools/chocolateyinstall.ps1'
+  './asyncapi-cli.nuspec'
+)
+
+foreach ($filePath in $filePaths) {
+  $fileContents = Get-Content $filePath
+  $fileContents = $fileContents -replace '{{version}}', $version
+  Set-Content $filePath $fileContents
+}
\ No newline at end of file
diff --git a/.github/workflows/deploy/chocolatey/tools/LICENSE.txt b/.github/workflows/deploy/chocolatey/tools/LICENSE.txt
new file mode 100644
index 00000000000..ba119f5d837
--- /dev/null
+++ b/.github/workflows/deploy/chocolatey/tools/LICENSE.txt
@@ -0,0 +1,207 @@
+
+From: https://github.com/asyncapi/cli/blob/master/LICENSE
+
+LICENSE
+
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+      any Contribution intentionally submitted for inclusion in the Work
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+      this License, without any additional terms or conditions.
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+      Contributor provides its Contributions) on an "AS IS" BASIS,
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+      whether in tort (including negligence), contract, or otherwise,
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+      Work (including but not limited to damages for loss of goodwill,
+      work stoppage, computer failure or malfunction, or any and all
+      other commercial damages or losses), even if such Contributor
+      has been advised of the possibility of such damages.
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+
+   Unless required by applicable law or agreed to in writing, software
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+
diff --git a/.github/workflows/deploy/chocolatey/tools/VERIFICATION.txt b/.github/workflows/deploy/chocolatey/tools/VERIFICATION.txt
new file mode 100644
index 00000000000..38590d5dfa0
--- /dev/null
+++ b/.github/workflows/deploy/chocolatey/tools/VERIFICATION.txt
@@ -0,0 +1,3 @@
+VERIFICATION
+Verification is intended to assist the Chocolatey moderators and community
+in verifying that this package's contents are trustworthy.
\ No newline at end of file
diff --git a/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1 b/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1
new file mode 100644
index 00000000000..13c7c049e3d
--- /dev/null
+++ b/.github/workflows/deploy/chocolatey/tools/chocolateyinstall.ps1
@@ -0,0 +1,42 @@
+$ErrorActionPreference = 'Stop' # stop on all errors
+$toolsDir   = "$(Split-Path -parent $MyInvocation.MyCommand.Definition)"
+
+$url          = 'https://github.com/asyncapi/cli/releases/download/v{{version}}/asyncapi.x86.exe'
+$url64        = 'https://github.com/asyncapi/cli/releases/download/v{{version}}/asyncapi.x64.exe' 
+
+$packageArgs = @{
+  packageName   = $env:ChocolateyPackageName
+  unzipLocation = $toolsDir
+  fileType      = 'EXE' 
+  url           = $url
+  url64bit      = $url64
+  #file         = $fileLocation NOTE: Commented out because we are using url instead
+
+  softwareName  = 'asyncapi-cli*' #part or all of the Display Name as you see it in Programs and Features. It should be enough to be unique
+
+  # TODO :- Change the checksum and checksumType to match the checksums for the above file.
+  # checksum      = ''
+  # checksumType  = 'sha256' #default is md5, can also be sha1, sha256 or sha512
+  # checksum64    = ''
+  # checksumType64= 'sha256' #default is checksumType
+
+  # MSI
+  # silentArgs    = "/qn /norestart /l*v `"$($env:TEMP)\$($packageName).$($env:chocolateyPackageVersion).MsiInstall.log`"" # ALLUSERS=1 DISABLEDESKTOPSHORTCUT=1 ADDDESKTOPICON=0 ADDSTARTMENU=0
+  validExitCodes= @(0, 3010, 1641)
+  # OTHERS
+  # Uncomment matching EXE type (sorted by most to least common)
+  silentArgs   = '/S'           # NSIS
+  #silentArgs   = '/VERYSILENT /SUPPRESSMSGBOXES /NORESTART /SP-' # Inno Setup
+  #silentArgs   = '/s'           # InstallShield
+  #silentArgs   = '/s /v"/qn"'   # InstallShield with MSI
+  #silentArgs   = '/s'           # Wise InstallMaster
+  #silentArgs   = '-s'           # Squirrel
+  #silentArgs   = '-q'           # Install4j
+  #silentArgs   = '-s'           # Ghost
+  # Note that some installers, in addition to the silentArgs above, may also need assistance of AHK to achieve silence.
+  #silentArgs   = ''             # none; make silent with input macro script like AutoHotKey (AHK)
+                                 #       https://community.chocolatey.org/packages/autohotkey.portable
+  #validExitCodes= @(0) #please insert other valid exit codes here
+}
+
+Install-ChocolateyPackage @packageArgs # https://docs.chocolatey.org/en-us/create/functions/install-chocolateypackage
diff --git a/.github/workflows/release-chocolatey.yml b/.github/workflows/release-chocolatey.yml
new file mode 100644
index 00000000000..b660240565c
--- /dev/null
+++ b/.github/workflows/release-chocolatey.yml
@@ -0,0 +1,50 @@
+name: Release Chocolatey Package
+on:
+  # We cannot run chocolatey release continusly every time we release something as sometimes we release a couple of times a day and overload chocolatey pipelines
+  # More details https://github.com/asyncapi/cli/issues/503
+  schedule:
+    - cron: '0 23 * * *' # Run every day at 23:00 UTC
+  # Since now release depends on schedule, might be that there is a situation we cannot wait for schedule and trigger release manually
+  workflow_dispatch:
+    inputs:
+      version:
+        description: 'Version to release (optional)'
+        required: false
+  
+jobs:
+  release:
+    name: Publish to Chocolatey Community
+    runs-on: windows-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+      - name: Set Version
+        id: release_version
+        run: |
+          if ( "${{ github.event_name }}" -eq "workflow_dispatch" -and "${{ github.event.inputs.version }}" -ne "" ) {
+            $version = "${{ github.event.inputs.version }}"
+          }
+          else {
+            $version = $(npm pkg get version)
+          }
+          echo "Setting version to $version"
+          echo "version=$version" >> $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 }}
+      - 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
+        with:
+          status: ${{ job.status }}
+          fields: repo,action,workflow
+          text: 'AsyncAPI CLI release to Chocolatey failed'
+        env:
+          SLACK_WEBHOOK_URL: ${{ secrets.SLACK_CI_FAIL_NOTIFY }}
\ No newline at end of file
diff --git a/docs/installation.md b/docs/installation.md
index 04d94400f2e..5b954799ca3 100644
--- a/docs/installation.md
+++ b/docs/installation.md
@@ -92,10 +92,40 @@ sudo installer -pkg asyncapi.pkg -target /
 ```
 
 ## Windows 
-For Windows just install the appropriate installer and simply follow the default installation steps to complete the installation process.
+
+There are two ways to install the AsyncAPI CLI on your Windows operating system: using the `chocolatey` package manager or executable files.
+
+### Chocolatey
+
+Prerequisites:
+[Chocolatey](https://chocolatey.org/install) must be installed on your Windows operating system. The installation instructions can be found [here](https://docs.chocolatey.org/en-us/choco/setup#installing-chocolatey-cli).
+
+To install the AsyncAPI CLI using the `chocolatey` package manager, run the following command in your terminal with administrator privileges:
+
+```sh
+# Install AsyncAPI CLI
+choco install asyncapi
+```
+
+To upgrade run this command:- 
+```sh
+# Upgrade AsyncAPI CLI
+choco upgrade asyncapi
+```
+To install a specific version run this command:
+```sh
+# Install AsyncAPI CLI version xx.xx.xx
+choco install asyncapi --version xx.xx.xx
+```
+All the AsyncAPI CLI versions can be found [here](https://chocolatey.org/packages/asyncapi).
+
+### Executable files
+
+Just install the appropriate installer and simply follow the default installation steps to complete the installation process.
 
 Download [asyncapi.x64.exe](https://github.com/asyncapi/cli/releases/latest/download/asyncapi.x64.exe) for 64-bit Windows and download [asyncapi.x86.exe](https://github.com/asyncapi/cli/releases/latest/download/asyncapi.x86.exe) for 32-bit Windows.
 
+
 ## Linux
 Selecting the appropriate AsyncAPI CLI installation method on a Linux operating system depends on your Linux distro.