[Azure] WinRM timeout with Windows 2016-Datacenter Marketplace Image

This issue was originally opened by @Dilergore as hashicorp/packer#8658. It was migrated here as a result of the Packer plugin split. The original body of the issue is below.

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Please refer the end of this thread to see other users complaining that this is not working.
https://github.com/MicrosoftDocs/azure-docs/issues/31188

Issue:

Started: December, 2019.
Packer cannot connect with WinRM to machines provisioned from Windows 2016 (2016-Datacenter) Marketplace image in Azure.

Further details:

WinRM timeout increase is not working. It seems the last image working is version: "14393.3326.1911120150" (Released 12th of Nov). It stopped working with "14393.3384.1912042333" (Released 10th of Dec).

This issue is only impacting 2016-Datacenter. 2019 is working properly.

To get image Details for a Region:

az vm image list --location northeurope --offer WindowsServer --publisher MicrosoftWindowsServer --sku 2016-Datacenter --all

URL to the Last Working Image:

https://support.microsoft.com/en-us/help/4525236/windows-10-update-kb4525236

URL to the Image where something went wrong:

https://support.microsoft.com/en-us/help/4530689/windows-10-update-kb4530689

Notes:

This is currently applying to North EU. I had no time to investigate in other regions but I believe the same images getting distributed to every region.

I am opening a Microsoft case and planning to update the thread with the progress.

[ThairAbdalla]

Hello,

we are seeing this issue in Azure US Gov Texas region for this
"os_type": "Windows",
"image_publisher": "MicrosoftWindowsServer",
"image_offer": "WindowsServer",
"image_sku": "2019-Datacenter",

we have tried with 2016-Datacenter and we get the same error message 

[dustingregory]

We are seeing the same with 2016-Datacenter on a "Standard_DS1_v2" vm_size in the east us. 2019-Datacenter seems to be working fine.

[dustingregory]

Here is debug output of what I'm seeing.

Packer version: 1.7.2 [go1.16.3 windows amd64]
packer-plugin-azure version: 1.0.1

==> azure-arm.Windows2016Azure: Waiting for WinRM to become available...
##[error]2021/08/11 11:15:32 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:32 [DEBUG] connecting to remote shell using WinRM
2021/08/11 11:15:33 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:33 [ERROR] connection error: unknown error Post "https://x.x.x.x:5986/wsman": remote error: tls: handshake failure
2021/08/11 11:15:33 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:33 [ERROR] WinRM connection err: unknown error Post "https://x.x.x.x:5986/wsman": remote error: tls: handshake failure
2021/08/11 11:15:38 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:38 [INFO] Attempting WinRM connection...
2021/08/11 11:15:38 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:38 [DEBUG] connecting to remote shell using WinRM
2021/08/11 11:15:38 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:38 [ERROR] connection error: unknown error Post "https://x.x.x.x:5986/wsman": remote error: tls: handshake failure
2021/08/11 11:15:38 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:38 [ERROR] WinRM connection err: unknown error Post "https://x.x.x.x:5986/wsman": remote error: tls: handshake failure
2021/08/11 11:15:43 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:43 [INFO] Attempting WinRM connection...
2021/08/11 11:15:43 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:43 [DEBUG] connecting to remote shell using WinRM
2021/08/11 11:15:43 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:43 [ERROR] connection error: unknown error Post "https://x.x.x.x:5986/wsman": remote error: tls: handshake failure
2021/08/11 11:15:43 packer-plugin-azure_v1.0.1_x5.0_windows_amd64.exe plugin: 2021/08/11 11:15:43 [ERROR] WinRM connection err: unknown error Post "https://x.x.x.x:5986/wsman": remote error: tls: handshake failure

[zsiebers]

Hello,

We are seeing the same issue here as well. first it was a 503 error and determined the listner was set to HTTP even though the winrm insecure parameter was set to true, we manually reset the listener to use http only and are now seeing the following error.

2021/09/10 14:16:55 packer.exe plugin: [DEBUG] connecting to remote shell using WinRM
2021/09/10 14:16:55 packer.exe plugin: [ERROR] connection error: http response error: 401 - invalid content type
2021/09/10 14:16:55 packer.exe plugin: [ERROR] WinRM connection err: http response error: 401 - invalid content type

[neeteshbhati]

Hope this helps.

I am using Windows Datacenter 2019 image and facing the same issue. After weeks of searching and debugging, the workaround mentioned at hashicorp/packer#8658 (comment) did the trick for me.

The WinRM connection works with the above configuration on an Azure VM but not on my system. I am assuming that has something to do with my company's network infrastructure/system port.