Post O365 Migration Quirkiness - Microsoft Community

hello everyone,

this going bit long 1 please bear me ... our desk stumped , i've been looking online no end now.  hopefully, can help.

• at work, on-prem our email , had single sign on.
• in april, migrated on o365.  once happened:
  • on desktop:
    • i had sign in second time outlook.  (i restart machine every day that's 2 logins per day unless shut down , restart outlook additional times.  it adds , it's annoying.)  my desktop windows 7 enterprise, sp 1, 64-bit.  office @ time office 2013.
    • emails arrived in inbox, hear alert, see preview see in inbox , not.  hitting send/receive nothing.  i have browse away inbox browse , new emails arrive.  it's intermittent can't reproduce it.  *grrr*
  • on laptop #1: (this exact environment desktop - test machine)
    • i 1 login using our single sign on, regardless of how many times launched outlook.  my laptop #1 windows 7 , office 2013.
  • on laptop #2:
    • i did 1 login using our single sign on, regardless of how many times launched outlook.  my laptop #2 windows 10 , office 2016.
    • the "invisible" emails occur on laptop well.  again, intermittent.
• in may, upgraded office 2016 on desktop , changed domain password.
  • on desktop, no difference in issues described above.
  • on laptop, have start logging in second time whenever launch outlook.  all other issues described above laptop remains.

solutions attempted (multiple times) include clearing credentials manager, recreating profile, , creating new "test" profile in outlook.  nothing worked - still have log in multiple times , of emails still arrive invisible until browse away , come back.  so ... ideas?  this has been driving me nuts since migration o365 last month.  any insight/guidance can provide appreciated!  thanks bunches!!

hi stormesixx,

understand experiencing 2 separate issues in outlook client after migrating office 365 , recommend post new thread regarding second issue in our forum can dedicated support each problem. , let’s focus on first issue in topic. time , cooperation.

first issue, i’d confirm following information:
1. please refer resolutions in article troubleshoot issue: 
a federated user repeatedly prompted credentials during sign-in office 365, azure, or intune
note: may need contact office 365 admin if not administrator.
2. how did migrate office 365? via cutover migration or other methods?
3. please take relevant screenshots password prompt , upload them our further check.
4. detailed version of adfs server. example: adfs 2.0 or adfs 3.0.

thanks,
sam

Office / Outlook / Other/unknown / Office 365 for business