Troubleshooting anything is a problem. If you don't have good troubleshooting skills, then you can spend all your time "wrapped around the axle" and accomplish nothing. If, on the other hand, you are skillful at troubleshooting anything, including Outlook Web Access (OWA), then you'll likely wind up solving most problems with relative dispatch.
While there are specific points to remember as you troubleshoot OWA, you should keep in mind a couple of general troubleshooting rules.
First: always check the last thing you did first.
This is only common sense. If everything was working, and then you "fixed" something, and now things aren't working right, then it's probable--well, not probable, certain--that the fix you applied caused the problem you now have. So always check first the last thing you did. This general troubleshooting rule applies to engines, boats, computers, hardware, software--anything you can think of.
Second, check your typing. If you are like me, you make lots of typing mistakes. That's fine if you're typing something like this tip, but computers don't know how to decide what you mean. They react to what you say, er, type. So check your typing.
That said, let's move on to OWA. If you have users who are having trouble logging into OWA, then there are some specific things to think about. These are listed in the Exchange documentation that you can find at Microsoft.com.
One change at a time—and keep a log
Make sure that you only change one setting at a time. If you do this, then you can keep a log of your changes. You should also write down any change in behavior that you see after you make each change. Keeping a log means that you will have a ready reference to know which changes affect what behavior. If you don't do this, then when you do fix the problem, or if you manage to muck things up totally, you won't know what happened, and you won't be able to back out of the situation you're in.
When you attempt to troubleshoot the problem, first create a new user account, and then enter a new user name and password for the server. If the authentication works with this new user name and password, which doesn't have any history of changes to the account settings, then you know that the problem is in the user's account settings, and you can go there and determine what the problem is.
Users don't have to input the full path to the OWA server to log on. But sometimes using the abbreviated path (like mailsystem.abccorp/exchange) will generate log on errors. If this is happening, then you should try logging on with the full pathname (like mailsystem.abccorp/exchange/jblow) to the server, whatever that is. If you can then log on using that full server pathname, the problem is likely to be with authentication.
If you have been able to log on with this new user account, then the authentication problem will likely be in the Active Directory settings for the user who is having trouble logging onto the OWA server. In this case, you need to go to the Active Directory properties for the user, or the group property object (GPO) for the user's group, to find out what the problem is. Here the troubleshooting can get tricky, but if you remember to make only one change at a time, and document the changes you make, you should find the problem fairly quickly by comparing the GPOs and property sheets for your new account with those for the user who is having the trouble.
And remember, always check the last thing you did first.
David Gabel has been testing and writing about computers for 25 years.