cloudflared is the Cloudflare Tunnel client which can be found here - https://github.com/cloudflare/cloudflared.

For those running cloudflared on Windows - Automatic updates is not currently possible as noted by Cloudflare here - https://developers.cloudflare.com/cloudflare-one/connections/connect-networks/downloads/.

Instances of cloudflared do not automatically update on Windows. 
You will need to perform manual updates.

This PowerShell script automates the check and/or update process for cloudflared on Windows.

The script checks for the latest version (using datecreated) on the cloudflared GitHub repository (https://github.com/cloudflare/cloudflared). The script compares the datecreated between the GitHub respository and the locally installed version. If a later version exists - the script will stop the cloudflared service and download and install the new version then start the cloudflared service again.

Ouputs are written to the console and the Event Viewer.

1. Requires PowerShell to be run as administrator.

2. Requires PowerShellForGitHub module (https://www.powershellgallery.com/packages/powershellforgithub) installed. Run Install-Module -Name PowerShellForGitHub.

3. Set CLOUDFLARED_INSTALL_PATH to the path of the locally installed cloudflared version.
   Example - "C:\Program Files (x86)\cloudflared\cloudflared.exe".

4. Register a new EventLog source in order for messages from the script to be written to the Application log in the Event Viewer.
   Run New-EventLog –LogName Application –Source “Update cloudflared”.
   Test the source is working by running - Write-EventLog –LogName Application –Source “Update cloudflared” –EntryType Information –EventID 1 –Message “HelloWorld”. The message should appear under the Application log in the Event Viewer.

5. Execute script as needed or setup a task using Task Scheduler in Windows for automatic updates.

PS C:\Scripts> .\update-cloudflared.ps1

---------------------------
cloudflared Windows Updater
---------------------------

Checking Github for cloudflared version ...
Latest cloudflared version -  4/06/2024 06:29:11

Checking installed cloudflared version ...
Installed cloudflared version -  8/05/2024 09:44:13

------------------------------
New cloudflared version found!
------------------------------
Update required ...
-------------------

Stopping cloudflared service ...
cloudflared service stopped successfully.

Downloading and installing latest cloudflared version from GitHub ...

    Directory: C:\Program Files (x86)\cloudflared


Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
-a----        16/06/2024     14:40       64393462 cloudflared.exe

Download and installation completed successfully.

Starting cloudflared service ...
cloudflared services start successfully.

PS C:\Scripts> .\cloudflared-auto-update.ps1

---------------------------
cloudflared Windows Updater
---------------------------

Checking Github for cloudflared version ...
Latest cloudflared version -  4/06/2024 06:29:11

Checking installed cloudflared version ...
Installed cloudflared version -  16/06/2024 14:40:33

Latest cloudflared version already installed. No update required!

PS C:\Scripts> .\update-cloudflared.ps1

---------------------------
cloudflared Windows Updater
---------------------------

Checking Github for cloudflared version ...
Latest cloudflared version -  4/06/2024 06:29:11

Checking installed cloudflared version ...
Installed cloudflared version -  16/06/2024 14:40:33

Latest cloudflared version already installed. No update required!

A new task can be created in Task Scheduler to check for and update cloudflared daily for example.

1. Create a Basic Task
2. Name - Update cloudflared
3. Task Trigger - daily
4. Action - Start a program
   Program/script - powershell
   Add arguments - -File "C:\Program Files (x86)\cloudflared\update-cloudflared.ps1"
5. Finish

Once created - edit the properties of the newly created Update cloudflared task. Under Security Options -

• Select - Run whether user is logged on or not
• Select - Run with highest privileges
• Enter Windows username and password when prompted

Run the newly created Update cloudflared task and check the Last Run Result shows (0x0) which means its sucessful.

Updated 19/06/2024 - update-cloudflared-telegram-notifications.ps1 is available which can now send a Telegram notification once the check and/or update is complete.

The following parameters are required for this -

  # Reference - https://docs.tracardi.com/qa/how_can_i_get_telegram_bot/

	$telegram_token=""
	$telegram_chat_id=""

A further parameter can also be configured to only send a Telegram notication when an update is required as opposed to a notification on every check.

$TELEGRAM_MESSAGE_UPDATES_ONLY = "true"

cloudflared Windows updater on ROOBER
GitHub cloudflared version checked - 06/18/2024 03:30:52

Installed cloudflared version checked - 05/08/2024 09:48:14

New cloudflared version found
Updated required!

-- Stopping cloudflared service
-- Downloading and installing latest cloudflared version from GitHub
-- Download and installation completed successfully
-- cloudflared service started successfully

cloudflared update complete