Outlook > GMail

[Koldov]

Microsoft Office LTSC Professional Plus 2024

 

Having some issues getting Outlook to connect to GMail... I have 4 GMail and 2 Exchange accounts to deal with so Outlook really is the best option for me. I also have 5 other members of staff that use it, so if this is a sign of things to come, I guess I'll need to know how to sort it out soon... 

 

Recently Outlook has been struggling to Send/Receive my various GMail accounts (fine with Exchange accounts).

 

Today it stopped completely and gave me the error that it couldn't connect to the server - We couldn't connect to the outgoing (SMTP) server.

 

I removed one of the accounts, but then it refused to add it back!

 

I've read some stuff about Google starting to requiring better authentication methods and I also read that this is possible with Outlook. I uninstalled Office Pro 2021 LTSC and installed Office Pro 2024 LTSC, thinking it might give me some different ways to authenticate, but no still the same interface without any other options and still the same error... Most of the instructions say:

 

1. Open Outlook and go to File: Navigate to the "File" tab in Outlook. 
    
2. Add Account: Click on "Add Account". 
    
3. Enter Gmail Address: Type in your full Gmail address. 
    
4. Connect: Click on "Connect" or "Continue". 
    
5. Google Sign-in: You'll be redirected to a Google sign-in page in your browse

 

But step 5 doesn't happen...

[Koldov]

"Starting May 1, 2025, Google Workspace accounts no longer support less secure apps, third-party apps, or devices that ask you to sign in to your Google Account with your username and password. You must use OAuth to let these apps and devices access your account. Third-party email apps that are no longer supported include Microsoft Outlook and the mail app on iOS and macOS. For detailed instructions and information, visit Transition from less secure apps to OAuth. For the latest dates, visit Google Workspace Updates."

 

Errr.... what?!

[OLPTech]

It's not great but at one of the schools I manage who uses Google Mail but some users love outlook we have this installed https://tools.google.com/dlpage/gssmo/ 

 

It is still working for them

[Koldov]

OK, so an update... and a contender for a post in the 'Annoying Things' thread!

 

After spending the day trying to sort this out, uninstalling and reinstalling Outlook  and getting many different and opposing answers from the internet, it seems that Outlook either can or cannot connect to a GMail account... trying to create 'app passwords' and looking for the 'less secure apps' setting in Google Workspace'... and that's without having to wade through all the 'Do you mean Outlook on the web...?' 'Do you mean O365...?' Do you mean New Outlook...?' Do you mean Outlook app for mobile...?'

 

Worse thing is after various attempts to uninstall Outlook and remove all trace from my computer, every time I reinstalled it, the same email accounts came up and tried to autodiscover using settings that I thought might be wrong (or in case I hadn't used the 'new' authorisation/verification methods when I originally set it up)... I couldn't seem to find where Outlook was getting these settings from, let alone how it still knew of them after I deleted pretty much every Outlook related file and registry setting I could find!

 

In the end I tried a new email account name so it didn't try to autodiscover and at least that came up with a 'Sign-In With Google' prompt, so I knew it was likely still possible. However, signing in to the GMail account still brought up the error that it couldn't connect...

 

However... over the weekend I thought I would give it another go and tried it on my laptop from home... just in case it might have been ISP or filtering issues at school. Opened up Outlook and it connected straight away, all accounts still connected and synced... no issues!

 

Came in this morning and did a final reinstall of Outlook on my computer and it found the accounts... this time when selecting them each one connected and synced without issue... I have also tested another user's Outlook that was having issues (which I only found out about on Friday afternoon) and that is OK this morning too!

 

W

 

T

 

F

 

🤬

 

So, what went wrong?

 

Glitch in the Matrix? Network issues? Outlook issues? Google issues?

 

No idea! 

 

I know you're probably going to say 'why don't you just use GMail?' but in all honesty I hate GMail... it looks like it was made by children, for children... I hate the interface, I hate the 'labels', I hate the way it orders conversations, I hate the way when you do get the conversation in the right order it throws you to the bottom of the thread to reply'... IMHO it's not an Enterprise worthy app for someone with 7 or 8 email accounts to manage....

Edited July 7, 2025 by Koldov

[Dos_Box]

I had the very same issue to the other week when I tried to connect a friends Outlook to their Gmail (none of which were corporate). Several hours of failing to connect to the account, despite all of the settings being correct (manually created), app passwords created and other faffing ensued.

I installed Thunderbird in the end. It connected first time.

[5nowman]

Hello!

 

ok things to try.

 

when it creates app password.. it is 16 characters with spaces right?

try with spaces

try without spaces

one of those should work

 

less secure devices... avoid. Google will switch it off at some point if not already off.

There are options to switch it back on... I would not recommend it.

 

I have had issues too. Hope that the google login page loads up in outlook... if that does it is also a good sign.

 

5nowman

 

[k-strider]

some of our users still prefer outlook we migrated from hosted exchange  to google workspace in 2020 but it is now the only mailbox they open (or delegated ones) and we use Google Workspace Sync for Microsoft Outlook (as mentioned earlier in the thread) https://tools.google.com/dlpage/gssmo/

 

it creates a profile in outlook and handles all the labels etc quite nicely - not sure if it would be a viable option when mixing different types of email accounts in outlook though.

Edited July 11, 2025 by k-strider