Tag: Outlook calendar not syncing

Best Outlook Calendar Synching Options

| July 23, 2026

Best Outlook Calendar Synching Options

Hi folks, below is a list of all the calendar synching options I can think of. These work with Outlook Classic. New Outlook has a completely different way of synching, so that will be for another time.

While I go through the list, I’ll also explain some calendar types you might have now and those options that come with. Video below.

Top of the list is of course, Microsoft Exchange

This type of account offers the best calendars in my opinion; it has so many benefits and is really worth the price. Besides just running smoothly in Outlook, it has all the functions of a PST file, but is better. Exchange allows the categories, colors, fields, sharing permissions, and many options that beat any other calendar. It also fully synchronizes with phones and other computers, iPad, tablets, etc.

IMAP (This computer only) calendars has less options

(This computer only) calendars are by far the worst calendar (natively only on your computer) and can often get deleted when someone deletes that Outlook profile it’s connected to. The file that manages the calendar is in an “OST” and can only be exported out via Outlook’s import/export feature. These files are extremely hard to back up and aren’t usually in any backup programs at all. OST files typically aren’t backed up by online programs like Carbonite, iDrive, etc. (you should check to see if these are). If you have IMAP now and want to have Exchange, please schedule time to chat about your migration.

The only solid option I know of is download Gsyncit from Fieldston. It is only for GMail IMAP users. Other folks with let’s say BlueHost, Network Solutions have to find something else. Some of my clients opt to use iCloud (read below) or move to Exchange.

POP/PST

These calendars in the PST are way better than the IMAP “This computer only” as they have most of the functions that the Exchange calendar has and the data is in a local PST file that can be backed up by online program, but they don’t have any synching options. iCloud is the best option if you have an iPhone. Gsyncit can be used if you have Gmail. Companion Link is a product I still see out in the wild.

iCloud calendars

This is the type of account I use for folks that have many different email types and have an iPhone and want to see and use their iPhone iCloud calendars.

Gmail users

I have a 3rd party program that I use to help sync Gmail IMAP and POP users with their Gmail calendars. The name is Gsyncit from Fieldston. It’s affordable and works great with (this computer only) and POP calendars.

I have a supporting podcast that goes more in depth if you want to listen (link below). Here are the simple explanations though, I cover these when I help clients who have calendar issues. If you want to synch your Outlook calendar and contacts with your phone, I can help with many options.

If you need my help, please use the link below to get in contact

 

Why is Outlook IMAP not syncing?

| May 30, 2026

Why is Outlook IMAP not syncing? Fix Outlook Email, Calendar, Contacts, and Microsoft 365 Sync Problems

–>Quick Answer:
Outlook may stop syncing because of OST corruption with IMAP or Exchange, damaged Outlook profiles, Microsoft 365 or App Password authentication failures, Gmail IMAP delays, iCloud conflicts, VPN interruptions, antivirus filtering, or Exchange Server connection issues.

Hi folks, this is my #1 request of all my Outlook calls. Outlook may stop syncing for 1000 reasons, but for you, it’s only probably only one and we need to figure that out. I’m a Microsoft Outlook Expert and I can help you with this request. I also work as a Microsoft 365 IT consultant.

This post will be about IMAP. For POP click here, Exchange not connecting click here and Google Workspace click here.

First, if you are using your email with IMAP configuration in Outlook, that list is way longer than a POP or Exchange account. Look in your Outlook and find out how your email is configured.

Let’s start by figuring out your account types. 

  1. Go to FILE in the upper left corner
  2. Click on Account Settings and it will drop down and click on Account Settings again.
  3. You will see how your emails are configured: POP, IMAP, Exchange or MAPI (Google Workspace)
  4. If not IMAP, use these reference links POP click here, Exchange click here and Google Workspace click here.

Common Reasons Outlook Stops Syncing IMAP

  1. Corrupted Outlook OST File (the OST is at its limit of 50 gigs)
  2. Damaged or corrupted Outlook Profile (very common, you will see “This Computer Only” folders)
  3. Mailbox needs refreshing/remapping (common for Network Solutions, HostGator, BlueHost)
  4. App Password required
  5. Antivirus (McAfee can do this more than any other)
  6. VPN is the biggest problem lately
  7. DNS Problems (misconfigured MX records)
  8. Domain issues (you need to update DNS for email delivery, or check to see if the bill is paid)
  9. Outlook Add-In Problems (rare but can happen on occasion)

Now you know the “whys” and hopefully this will help you try to figure it out, I can help too if you’d like to schedule an appt.

Keep in mind that IMAP synching can be a longer request to complete. Typical is 1-2 hours of billable time and many calls. I will also back up all your data and complete a full onboarding before starting. This is important to do and also something amateurs don’t often do. Hiring an experienced Outlook master technician like me will get the job done using best practices. Side note: Often clients opt to move to a Microsoft Exchange server instead of repairing their Outlook profile. This will be covered in your onboarding.

Why is Outlook not syncing?

| May 30, 2026

Why is Outlook not syncing? Fix Outlook Email, Calendar, Contacts, and Microsoft 365 Sync Problems

–>Quick Answer:
Outlook may stop syncing because of OST corruption with IMAP or Exchange, damaged Outlook profiles, Microsoft 365 or App Password authentication failures, Gmail IMAP delays, iCloud conflicts, VPN interruptions, antivirus filtering, or Exchange Server connection issues.

Hi folks, this is my #1 request of all my Outlook calls. Outlook may stop syncing for 1000 reasons, but for you, it’s only probably only one and we need to figure that out. First, if you are using your email with IMAP configuration in Outlook, that list of reasons why is way longer than a POP or Exchange account. I’m a Microsoft Outlook Expert and I can help you with this request. I also work as a Microsoft 365 IT consultant.

This post will be about IMAP. For POP click here, Exchange not connecting click here and Google Workspace click here.

First, if you are using your email with IMAP configuration in Outlook, that list is way longer than a POP or Exchange account. Look in your Outlook and find out how your email is configured.

Let’s start by figuring out your account types. 

  1. Go to FILE in the upper left corner
  2. Click on Account Settings and it will drop down and click on Account Settings again.
  3. You will see how your emails are configured: POP, IMAP, Exchange or MAPI (Google Workspace)
  4. If not IMAP, use these reference links POP click here, Exchange click here and Google Workspace click here.

Common Reasons Outlook Stops Syncing IMAP

  1. Corrupted Outlook OST File (the OST is at its limit of 50 gigs)
  2. Damaged or corrupted Outlook Profile (very common, you will see “This Computer Only” folders)
  3. Mailbox needs refreshing/remapping (common for Network Solutions, HostGator, BlueHost)
  4. App Password required
  5. Antivirus (McAfee can do this more than any other)
  6. VPN is the biggest problem lately
  7. DNS Problems (misconfigured MX records)
  8. Domain issues (you need to update DNS for email delivery, or check to see if the bill is paid)
  9. Outlook Add-In Problems (rare but can happen on occasion)

Now you know the “whys” and hopefully this will help you try to figure it out, I can help too if you’d like to schedule an appt.

Keep in mind that IMAP synching can be a longer request to complete. Typical is 1-2 hours of billable time and many calls. I will also back up all your data and complete a full onboarding before starting. This is important to do and also something amateurs don’t often do. Hiring an experienced Outlook master technician like me will get the job done using best practices. Side note: Often clients opt to move to a Microsoft Exchange server instead of repairing their Outlook profile. This will be covered in your onboarding.