RSSCategory: Outlook Support

Be careful when using Ai to fix your own Outlook and 365 issues

| October 1, 2026

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”

If you need my help, please use the form below to get in contact. Or email lisa@callthatgirl.biz or call 612-865-4475

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

  1. 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. 
  2. 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. 
  3. 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. 
  4. 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.
  5. 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. 
  6. 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. 
  7. 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. 
  8. 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. 
  9. 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
  10. 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.

 

SPF DKIM and DMARC Help for for Small Business Microsoft 365

| September 29, 2026

SPF, DKIM, and DMARC Help for for Small Business Microsoft 365

Clients often call me to help with these DNS records as they can be complicated to figure out, and if you update them wrong…it could delay your email to work correctly.

I offer by the hour, no contract consulting for small business clients using Microsoft 365.

If you need help, please use the form below to get in contact.

I can help review and troubleshoot:

    • Microsoft 365 SPF records
    • DKIM setup and activation
    • DMARC records and policies
    • Multiple services sending from one domain
    • Duplicate or conflicting SPF records
    • Email marketing authentication
    • Domain and DNS configuration errors

Gmail Outlook Sync Expert

| September 9, 2026

Gmail Outlook Sync Expert

I’ve been supporting Gmail and Outlook since the day users could have problems with Gmail and Outlook, basically since 2004. But I got more experienced when I started my own business in 2007. I was helping users at their homes with all computer repair and of course, a lot of email help. Back then, it was way different. We only had POP and I don’t remember supporting IMAP until around 2010 maybe. POP was the thing and we all popped down our emails into Outlook if you weren’t on a corporate server. A good percentage of my work was Gmail/Google Workspace until recently, things are smoothing out a bit better but I’m still taking a lot of calls for Gmail/Outlook. My number one call? Fixing Synchronizing issues.

Fun fact: Many people with synchronzing errors in Outlook using Gmail could get rid of this problem by setting up another account type for Google in Outlook. Ask me how I can help with this, it can sync everything in your Google account for email, calendar and contacts! 

Common problems I help repair, fix or solve with Gmail and Outlook

As a Gmail and Outlook expert, I help home users, executives, professionals, and small businesses with nearly every type of Gmail issue, including setting up Gmail and Google Workspace accounts in classic Outlook and New Outlook, repairing sending and receiving problems, (this computer only) folders, calendar and contacts, repeated password prompts, authentication failures, IMAP and SMTP errors, missing or duplicated messages, incorrect folders and labels, Outlook search problems, calendar and contact synchronization, missing autocomplete addresses, multiple Gmail accounts, aliases, and Outlook profiles.

I also troubleshoot Gmail across Windows computers, Macs, iPhones, iPads, and Android devices; organize confusing personal and business email environments; recover and import old email; transfer contacts and calendars; configure new computers; and help clients migrate from Gmail or Google Workspace to Microsoft 365. Before changing anything, I determine where the important email and data are stored, identify which accounts and profiles control them, explain the problem in plain English, and work toward a reliable setup that fits how the client actually uses email.

And I perform migrations for clients from Google Workspace to Microsoft 365.

I work by the hour, typical repair for a full rework is 2 hours (2-3 appts that are usually under an hour each time).

Before I help each client, I do a review of their accounts, systems and create a game plan and make back ups of all the data involved (email, calendar, contacts, notes, tasks) and then I start work.

If you need my help, feel free to use the form below or call 612-865-4475 or email lisa@callthatgirl.biz

 

Gmail Outlook Specialist

| September 9, 2026

Gmail Outlook Specialist

I’ve been supporting Gmail and Outlook since the day users could have problems with Gmail and Outlook, basically since 2004. But I got more experienced when I started my own business in 2007. I was helping users at their homes with all computer repair and of course, a lot of email help. Back then, it was way different. We only had POP and I don’t remember supporting IMAP until around 2010 maybe. POP was the thing and we all popped down our emails into Outlook if you weren’t on a corporate server. A good percentage of my work was Gmail/Google Workspace until recently, things are smoothing out a bit better but I’m still taking a lot of calls for Gmail/Outlook.

Fun fact: Did you know that many domained Google users are still using IMAP? These account set ups don’t synch the calendar or contacts. Ask me how to set up the correct account so you can view everything on your Google account with Outlook! 

Common problems I help repair, fix or solve with Gmail and Outlook

As a Gmail and Outlook expert, I help home users, executives, professionals, and small businesses with nearly every type of Gmail issue, including setting up Gmail and Google Workspace accounts in classic Outlook and New Outlook, repairing sending and receiving problems, (this computer only) folders, calendar and contacts, repeated password prompts, authentication failures, IMAP and SMTP errors, missing or duplicated messages, incorrect folders and labels, Outlook search problems, calendar and contact synchronization, missing autocomplete addresses, multiple Gmail accounts, aliases, and Outlook profiles.

I also troubleshoot Gmail across Windows computers, Macs, iPhones, iPads, and Android devices; organize confusing personal and business email environments; recover and import old email; transfer contacts and calendars; configure new computers; and help clients migrate from Gmail or Google Workspace to Microsoft 365. Before changing anything, I determine where the important email and data are stored, identify which accounts and profiles control them, explain the problem in plain English, and work toward a reliable setup that fits how the client actually uses email.

And I perform migrations for clients from Google Workspace to Microsoft 365.

I work by the hour, typical repair for a full rework is 2 hours (2-3 appts that are usually under an hour each time).

Before I help each client, I do a review of their accounts, systems and create a game plan and make back ups of all the data involved (email, calendar, contacts, notes, tasks) and then I start work.

If you need my help, feel free to use the form below or call 612-865-4475 or email lisa@callthatgirl.biz