Skype for Business asks me to log in every time it starts, even if I ask it to keep me signed in

Hi,

Make sure that you Skype for Business client is updated, there was an old problem with this in an old version.

Try to delete your profile as the next step.

Delete your sip profile folder: Skype for Business:

1. Exit skype for business, Close Skype for Business completely by right-clicking the skype for business icon in the Windows System Tray and selecting Exit. Also make sure that Outlook is closed.
2. Open Windows Explorer and navigate to the folder that holds your profile.
   %LocalAppData%\Microsoft\Office\16.0\Lync
3. Delete the sip_username directory that matches the sip address of the user experiencing the issues.  This directory will be rebuilt when client is restarted the next time.
4. Restart the computer.

Try remove the credential to check if the issue persists:

1. Click Start, click Control Panel, and then click Credential Manager.
2. Select Windows Credential section click on your Skype for Business credential.
3. Click Remove (you can remove all Skype for Business cache, and re-enter the credential).