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Cached exchange mode causing password prompts

We have been trying to deal with this password prompt for quite a while now and for a period of time we were pointing the blame to a few add-ins. However, during today's troubleshooting I ran a status test to see what it was trying to connect to during the time of the prompt. Well I found a connection that stood out where it was trying to connect in cache mode. I decided to turn cached exchange mode off and ever since then I have not gotten a password prompt. After restarting outlook about 50 or so times I decided it was enough and tried to re-enable the cached exchange mode, and as I expected, the password prompts started coming back.

So what could be causing cached exchange mode in outlook H&B 2016 to to prompt for these windows credentials? I saw one spiceworks article where a guy was basically saying that cached mode might be connecting the public FQDN instead of the private network name and it prompts because it sees the server as being outside of the logged in domain? Just looking for a possible resolution so that we can still keep exchange mode enabled for the benefits it provides.
ExchangeOutlookTroubleshooting

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Steve

8/22/2022 - Mon
Danilo Andrade

Have you tried the resolution described on this article from Microsoft?
https://support.microsoft.com/en-us/help/2984912/outlook-continually-prompts-for-your-password-when-you-try-to-connect

You can give Office 365 troubleshooting assistant a try and see what more detailed information you get. If needed, post the results here:
https://diagnostics.outlook.com/#/
Steve

the only realistic differences between cached and online mode is the downloading of things like offline address books. That is the starting point I'd recommend checking settings around that to see if youve got the OAB URLs set incorrectly. let us know what exchange/o365 version youre using and we may be able to point you in the right direction.
Infinity Solutions

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We are using office home and business 2016 and exchange 2013
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Steve

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