iPad + Tailscale Issues

Hello,

Thank you for reaching out. At first glance, we don’t have a clear idea of where the issue might be coming from. We’ll try to reproduce the problem in a similar setup on our side to investigate further.

Once we have more information, we’ll get back to you with our findings.

Best regards,

Hi,

After configuring a Tailscale environment on our end, we were unable to reproduce the issue you are encountering.

To assist further, could you please provide the following information:

• Your iPad model
• The exact version of Tailscale installed
• Whether your iPad is managed via MDM and if any per-app VPN profile is configured
• Whether you are using an exit node in Tailscale
• The result of testing a brand-new SSH entry in RDM that points directly to the Tailscale IP (same IP/port as used in Termius, with no gateway or additional options)
• Whether the issue occurs on different networks (e.g., LTE vs Wi-Fi)
• Whether the issue occurs on other devices as well

It may also be helpful to try a brand-new setup with minimal configuration changes.

The fact that you are able to ping the Tailscale IP from RDM but cannot connect to it is unusual. Could you please reproduce the issue and send us your application logs?
To do so, open the main menu > Help and Support > Application Logs > Clear Logs. Then attempt to open your RDP and/or SSH entry and go to Help and Support > Submit a Support Ticket to send us the logs.

Thank you in advance for your cooperation.

Best regards,

Hi,

After configuring a Tailscale environment on our end, we were unable to reproduce the issue you are encountering.

To assist further, could you please provide the following information:

• Your iPad model
• The exact version of Tailscale installed
• Whether your iPad is managed via MDM and if any per-app VPN profile is configured
• Whether you are using an exit node in Tailscale
• The result of testing a brand-new SSH entry in RDM that points directly to the Tailscale IP (same IP/port as used in Termius, with no gateway or additional options)
• Whether the issue occurs on different networks (e.g., LTE vs Wi-Fi)
• Whether the issue occurs on other devices as well

It may also be helpful to try a brand-new setup with minimal configuration changes.

The fact that you are able to ping the Tailscale IP from RDM but cannot connect to it is unusual. Could you please reproduce the issue and send us your application logs?
To do so, open the main menu > Help and Support > Application Logs > Clear Logs. Then attempt to open your RDP and/or SSH entry and go to Help and Support > Submit a Support Ticket to send us the logs.

Thank you in advance for your cooperation.

Best regards,

@Nicholas Lachapelle

Hey -

Thanks for taking a look!

• iPad is an iPad Pro 12.9 3rd gen running iPadOS 26.1 with no MDM, etc running and no per-app VPN config that I’m aware of
• Tailscale is 1.90.4 and no exit node is being used
• Making a new ssh session entry with nothing but the host IP defined results in the same behavior
• I tried connecting to the same RDM connection on a Windows box with Tailscale installed and it worked fine
• All tests conducted via “WiFI” (mobile hotspot from phone), I’ll test on more traditional WiFi when I get a chance

Submitted a ticket with logs, but I took a look, and it didn’t seem to log much.

Again, much appreciated. If y’all can’t reproduce this on an iPad (or anyone else out there) it very well could be something on my end.

Hi,

We appreciate the detailed answer and taking the time to send your logs.

From your logs, we can clearly see the connection failing from the beginning. Considering you can connect using other apps, I tend to believe the issue isn't Tailscale. Here's a quick list of things I would double-check:

• In your iOS settings, make sure you see RDM in Privacy & Security > Local Network and that it is enabled.
• Confirm the port is correct in your connection settings.
• Confirm the connection details are the same as the ones you used in other apps.
• Is your Tailscale IP IPv4 or IPv6?

You mentioned you tried connecting to the same connection on a Windows box.

• Do you mean you tried the same entry on RDM Windows? If so, was it a virtual machine?
• Did you use the same data source to connect through the same entry?
  • If you created the SSH entry on an iPad, I would try creating a new one on Windows (or any other RDM platform) and check if the issue is resolved when connecting from both devices.
• Have you tried other mobile devices? If you have access to another iPad or cellphone (Android included), we might find a pattern or a different outcome.

In your original post, you mentioned the behaviour is the same on RDP. Could you repeat the process of sending us the logs with RDP included? You can enable RDP logging beforehand by opening the RDM settings, then Sessions > RDP > Enable logging.

If you wish, we can schedule a live session with the support team at a time that is best for you.

Thank you again for your cooperation.

Best regards,

I wanted to add a quick note here (sorry about the delay!)

I was finally able to test the iPad/Tailscale setup via a proper wifi connection and it DOES work using the Tailscale IP from the iPad over wifi while the iPad is connected to Tailscale VPN with nothing else changed. Generally, the iPad is connected via personal hotspot from my phone and out to the cell network, so something in that situation seems to be the root cause.

I'm not entirely sure why other iPad based apps don't have issues when used that way, but this should narrow down the scope of the issue a lot. This is fairly edge case, so I completely understand if it's not something y'all want to work on.

Thanks!

Hi,

Unfortunately, we were unable to reproduce the issue on our end. However, I did find something that might be worth checking in your Tailscale configuration. Based on discussions in the Tailscale GitHub, please double-check your "VPN On Demand" settings in Tailscale. Since you're using a hotspot to connect from your iPad to your remote desktop, also ensure that Tailscale is properly connected on the iPad while using the hotspot.

At this point, as we cannot reproduce the behaviour and it appears to be related to your VPN or cellular network environment, there is nothing further we can realistically adjust on the RDM side. If you are eventually able to identify a specific Tailscale or carrier configuration that consistently causes this issue with RDM while other apps continue to work, please feel free to share the details and we will gladly review them.

Best regards,