We help IT Professionals succeed at work.

Hoist the colors! We’ve added location flags to usernames sitewide, so it's easier to connect with the global community on EE. View My Profile

x
Troubleshooting Question

Cached exchange mode causing password prompts

136 Views
Last Modified: 2020-08-17
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.
Comment
Watch Question

Danilo AndradeIT Systems Analyst

Commented:
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/#/
SteveArchitect/Designer
CERTIFIED EXPERT

Commented:
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 SolutionsData, Voice, Internet Services

Author

Commented:
We are using office home and business 2016 and exchange 2013
Architect/Designer
CERTIFIED EXPERT
Commented:
This one is on us!
(Get your first solution completely free - no credit card required)
UNLOCK SOLUTION

Gain unlimited access to on-demand training courses with an Experts Exchange subscription.

Get Access
Why Experts Exchange?

Experts Exchange always has the answer, or at the least points me in the correct direction! It is like having another employee that is extremely experienced.

Jim Murphy
Programmer at Smart IT Solutions

When asked, what has been your best career decision?

Deciding to stick with EE.

Mohamed Asif
Technical Department Head

Being involved with EE helped me to grow personally and professionally.

Carl Webster
CTP, Sr Infrastructure Consultant
Empower Your Career
Did You Know?

We've partnered with two important charities to provide clean water and computer science education to those who need it most. READ MORE

Ask ANY Question

Connect with Certified Experts to gain insight and support on specific technology challenges including:

  • Troubleshooting
  • Research
  • Professional Opinions
Unlock the solution to this question.
Join our community and discover your potential

Experts Exchange is the only place where you can interact directly with leading experts in the technology field. Become a member today and access the collective knowledge of thousands of technology experts.

*This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

OR

Please enter a first name

Please enter a last name

8+ characters (letters, numbers, and a symbol)

By clicking, you agree to the Terms of Use and Privacy Policy.