Be careful when using Ai to fix your own Outlook and 365 issues
Hi folks, I believe you found this post from my newsletter or from my blogs while you’re out searching for help. Many people are now coming to my site from Ai sources and I love that! AI is an amazing troubleshooting assistant. And I use ChatGPT every day, it’s so helpful for me but with marketing. But, I rarely use Ai to troubleshoot problems, very rarely and only when I am in a deep dive on a very difficult problem. What I do is put in all my information and then read the summaries and since I know Outlook very well, I can assess if that will help or not. But AI doesn’t have to deal with the consequences if the fix goes sideways, you do. Before deleting data, changing DNS, running PowerShell or changing Microsoft 365 security settings, make sure you understand exactly what you’re changing. I am always preventative and tell you what can happen, why we need to backup, what can change, anything important. My favorite line is “A client being told to hack the registry by Ai trying to fix a problem is like me trying to give myself a root canal. Not happening”
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Here are my 10 things to be careful with when using Ai to fix your own issues: (and yes, Ai knows my work well, so it created this list, with my approval of course)
Top 10 Things to Be Careful About When Using AI to Fix Tech Problems
- Deleting Outlook PST, OST, or other data files
AI may suggest deleting or recreating a file to fix Outlook. Before deleting anything, make sure you know what the file contains and whether the data exists somewhere else. A PST, in particular, can contain the only copy of older email. Quick Answer: Back up anything before doing anything. - Changing Microsoft 365 security settings
Be extremely careful when AI tells you to change MFA, Conditional Access, authentication methods, security defaults, Entra ID settings, or admin roles. One wrong change can potentially lock you out and me out too maybe. I can only fix problems if I can log in. Quick Answer: Do you have a backdoor account if the main account can’t get in? This is how I can help. - Changing DNS records
MX, SPF, DKIM, DMARC, CNAME and other DNS records affect important services. Don’t blindly replace or delete records because AI says they’re wrong. A bad DNS change can cause email delivery failures or other services to stop working. Ai doesn’t know what you really have going on with your accounts, other emails connected, other domains connected, aliases, licenses, etc. Quick Answer: So be careful, I can help here if you need it. - Running PowerShell commands you don’t understand
AI can produce very convincing PowerShell commands. Before running one, understand exactly what it changes, especially commands affecting Exchange Online, Entra ID, mailboxes, permissions, retention or users. Quick Answer: I don’t even know how to run PowerShell and have never needed to run it, so you should probably not ever need to use it either. It’s not for everyone, it’s for experienced technicians in my opinion. - Deleting Outlook profiles or removing accounts
“Remove the account and add it back” is common troubleshooting advice. Sometimes that’s appropriate—but first determine where the user’s data, contacts, calendars and archives are actually stored. Quick Answer: Ai might help here with the list of things to do, but I don’t delete profiles EVER. Save that information as the new profile might not capture it and if you delete, there is no going back usually. - Uninstalling or resetting Microsoft Office
Repairing or reinstalling Office can help with certain problems, but it shouldn’t automatically be Step #1. It can also introduce additional issues while doing nothing about a problem that’s actually caused by the Outlook profile, Windows profile, Exchange, add-ins or Microsoft 365. Quick Answer: I rarely reinstall Office for Outlook issues, synching, opening and other issues are other problems typically. - Changing registry settings
If AI gives you a registry path and says, “Change this value,” don’t assume it’s safe. Registry changes can affect Outlook, Office and Windows behavior, and AI may provide instructions that are outdated or inappropriate for your particular version. Quick Answer: Most people think that expanding the size of a PST to 100 gigs will solve a problem, I tend to focus on longer term solutions. The Reg fix will only last so long and can be a complete disaster later on. - Following instructions for the wrong Outlook
This is a BIG one now. Classic Outlook and New Outlook are different products. Instructions for Classic Outlook may not apply to New Outlook, and menus/settings can also vary between Microsoft 365 versions. Quick Answer: New Outlook is still so new that many searches on the internet aren’t updated quite yet. I have seen a lot of issues with New Outlook and have to reverse clients back to Outlook Classic due to performance. - Assuming AI understands your entire environment
AI only knows what you’ve told it. It doesn’t automatically know your Microsoft 365 tenant configuration, licenses, DNS provider, Exchange configuration, security policies, third-party filtering, backups or how your company is set up. One missing detail can completely change the correct troubleshooting path. Quick Answer: Many important factors are missed and it’s due to just the end user not knowing potentially.Example: Ai would never know if you’re using a 3rd party app that broke your Outlook or if you got hacked - Making changes without a backup or rollback plan
This is probably the biggest lesson. Before I make a potentially destructive change for a client, I want to know: What am I changing? What could it affect? Can I undo it? Is the client’s data protected first? AI troubleshooting should follow the same rule. Quick Answer: I almost never do a system restore anymore to fix Outlook issues. In fact, it’s been years.
Category: Outlook Support
About the Author (Author Profile)
Lisa Hendrickson is the owner of Call That Girl. She is an Outlook Expert and Microsoft 365 Consultant.Subscribe
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