Jump desktop not loading before login Catalina 10.15.4

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Wolfgang Loss-Wells

So I have the latest version of jump desktop connect, and just updated to the latest point release of Catalina. I can no longer connect remotely before login and have to manually launch jump desktop connect on the machine in order to access it remotely.

Effectively this means I can no longer reboot the machine from remote.

I am very glad I only upgraded 1 out of my 5 machines to Catalina. What a nightmare.

Any ideas on what I can try to get the service auto launching prior to login?

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    James

    I have the exact same problem/request only all my machines are on Catalina and I am effetely useless :-(

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    Jump Desktop Support

    Hi. This is not a known issue with Catalina 10.15.4 and Jump Desktop. Can you please let me know if you see any error messages when you try to connect to a freshly booted machine? What do the error messages say?

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    James (Edited )

    It's happening on all my Catalina 10.15.4 machines.

     

    On the machine, I see a login prompt.  On JumpDesktop I see a spinning. wheel on a blank screen, followed by the "Computer is offline" message.

    One of my machines is a brand new install with only Jumpdesktoip (and SOPHOS home) installed so no other influences.

     

    As soon as as the account is logged in, JumpDesktop works.

    This is also true for machines with multiple accounts (each account must be logged in for JumpDesktop to work on that account).

    Maybe this is a new issue with 10.15.4?

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    Wolfgang Loss-Wells

    In my case after rebooting the remote machine behaves as if it is offline (greyed out in the interface). I have to physically login and launch the jump desktop connect app in order for my remote machines to be able to connect. This is the case for both my iOS and macOS client apps.

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    Jump Desktop Support

    Hi Wolfgang - can you please open up Jump Desktop Connect -> Settings -> General and make sure 'Start when computer starts' is CHECKED?

     

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    James

    Hi Wolfgang,

    Are you also on 10.15.4?

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    Wolfgang Loss-Wells (Edited )

    I am on the latest update of Catalina. I believe it's 10.15.4.1.

     

    And yes "start when computer starts" is checked.

     

    I should add that the Mac in question is very rarely rebooted, so it's possible that this is an issue with earlier versions of Catalina as well and I just never realized.

    I should also add that I tried reinstalling connect already.

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    James

    Latest is 10.15.4 as of a few days ago.

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    Wolfgang Loss-Wells (Edited )

    I guess I got confused. I believe there was a supplemental update to 10.15.4. Either way this last update of macOS has a lot of bad feedback online. I will test a downgrade to 10.15.3 tonight.

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    James

    :-)

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    Jump Desktop Support

    @Wolfgang - do you have any third party security products installed on the Mac?

    Thanks.

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    Wolfgang Loss-Wells (Edited )

    I do not have any security products installed on my Mac with the exception of Little Snitch, which is configured to allow all connections. I also can report back that reverting to the previous release of Catalina is too time consuming for me to do at this time.

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    James

    Wolfgang, do you have FileVault enabled?

    I did.  I have just turned it off and now Jump Desktop works fine between restarting and logging in.

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    Jump Desktop Support

    @James That's really strange. All our test machines have Filevault enabled and it works. When you had Filevault enabled, was it booting to the login screen after the Filevault prompt or straight into the user's account and after which you logged off?

     

    Thanks.

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    James (Edited )

    With FileVault enabled, it would boot straight to the login screen (without any FileVault prompt).

    Only after login would Jump Desktop start to work.  ...but isn't that because I need to login to "decrypt" my data?

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    Jump Desktop Support

    Okay - so you were seeing 2 login prompts after a reboot, right:

    1. Right after reboot - a prompt to unlock the machine.

    2. Then the login window where the user actually logs in?

    My understanding is after prompt 1 above, the entire disk is unlocked from that point on.

     

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    James

    No!

    I have edited my last reply to make it clearer.

    I was only ever seeing my normal login prompt.

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    James

    OK,  this is 100% something to do with FileVault.

    I just switched it back on, and again I could not logon with Jump Desktop after restarting.  Looking at the local monitor, it was sitting happily at the login screen.

    I then switched FileVault back off, and Jump Desktop worked a couple of seconds after it booted up (showing the login screen).

    The only thing I haven't tried (or should note) is that I was using FileVault with my iCloud ID, not with a separate recovery password.

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    Jump Desktop Support

    Ok - so there a way to configure FileVault to not log you in to your desktop - but we're going to skip that because I don't think you've done this.

    Now: With FileVault enabled, when you reboot - the computer should be marked as OFFLINE in Jump when you see the FileVault login prompt. Do you see this?

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    James

    I am not sure what you mean by FileVault login prompt.

    With FileVault enabled, after a reboot I see the *normal* login prompt on the local monitor.  At this point Jump shows the Mac as offline.

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    Jump Desktop Support

    @James Right - sorry about the confusing terminology. So you are right: When you have FileVault enabled and you restart the machine, the disk will be encrypted completely - at that point nothing can / is running except a very, very minimal shell of macOS which prompts you for your password. When you enter the password, macOS uses that to unlock the disk and proceed to load the OS - which happens to include Jump. So this is expected - though this hasn't changed in Catalina. This is something that's always been there since FileVault 2 was released in macOS 10.9.

    Also useful tip: if you want to reboot a Mac without the FileVault prompt getting in the way, on the command line use this: fdesetup authrestart

     

     

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    James

    OK, thanks.  So not being able to restart an unattended remote machine with FileVault enabled is expected behaviour?

    Are you saying that the workaround to this is to use the command "fdesetup authrestart" which allows me to restart an unattended FileVault enabled Mac remotely and still get Jump to work?  ...so my only problem only arises with a power cut or an unexpected reboot?

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    Wolfgang Loss-Wells

    I also have filevault enabled on the Catalina machine. The strange thing is on my iMac which is running Mojave, and also has file vault enabled, I do not have this problem.

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    Jump Desktop Support

    > So not being able to restart an unattended remote machine with FileVault enabled is expected behaviour?

    Not exactly: You can restart it, but you need a way to unlock the disk _before_ the restart to make sure the OS loads up. If the disk is locked, nothing on the machine runs (including Jump or any other apps you've installed) until the disk is unlocked.

    > workaround to this is to use the command "fdesetup authrestart" 

    Right - this command is used to unlock the disk _before_ the restart.

    > so my only problem only arises with a power cut or an unexpected reboot?

    Correct. Unfortunately with full disk encryption - this is how it works. This is not a Mac limitation - this is how it works on Windows as well.

     

     

     

     

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    Jump Desktop Support

    @Wolfgang - after your restart the Catalina machine - is the computer marked as 'offline'?

     

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    Wolfgang Loss-Wells

    Yes the Catalina machine is marked as offline after restart. I have no issues rebooting my Mojave machine that has file vault enabled. 

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    Jump Desktop Support

    @Wolfgang: I  can't think of a way where Jump Desktop would work on Mojave if you have FileVault enabled and you restart the machine. Can you double check for me please to make sure FileVault is actually enabled?

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    Wolfgang Loss-Wells

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    Jump Desktop Support

    @Wolfgang - thanks for that. What happens when you restart your Mojave Mac? Do you see the login screen or are you taken straight to your desktop?

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    Wolfgang Loss-Wells (Edited )

    I get a login screen at reboot. I should clarify that I don't have to do a separate FileVault "unlock" login to get in on either of my machines.

     

    I have seen that in the past. But maybe I changed something in the system? I honestly don't remember.

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