Forum Discussion
Gmail workspace and new Outlook sync problems
Hi there,
We are a hybrid Office 365 (desktop apps, intune, defender) and Google workspace (emails, files, calling). we have been using Google outlook (GWSMO) for years and it has always been problematic. late in 2024 we were happy that classic outlook can connect to gmail using oauth2 natively without using the addin, but calendar synch and contacts synch did not exist.
Earlier this year we were happy that the new outlook has solved this problem and started to migrate our users to the new outlook from may 2025. Really happy about that.
Our outlook version currently is:
Microsoft Outlook Version: 1.2025.806.300 (Production)
Client Version: 20250822005.29
WebView2 Version: 139.0.3405.125
What we have been noticing recently is that some users are getting delayed emails that can be a couple of hours.
We have also noticed that when toggling offline mode to off (or on) they are getting delivery errors saying it cannot be delivered. after a few attempts it goes through but a draft copy stays in the outbox.
We have seen a similar issue in a forum about delayed email here and we will try the options given as well doing the obvious by pressing the sync button:
https://answers.microsoft.com/en-us/outlook_com/forum/all/new-outlook-not-syncing-with-gmail-no-error/e97349d3-27dc-4313-b905-2657b0a36784
what I would like to do is see if we can get the logs from outlook for connections. Does anyone know where that is stored?
10 Replies
C:\Users\LisaE\AppData\Local\Microsoft\Olk\logs
This is where mine are.
Btw...I haven't seen any issues with Gmail/GW having issues with security on the accounts in New Outlook but that could be something to look at. As well the connector might need to be disconnected on the Google side and try adding it again.
Let me ask you this, since all of these issues seem to be sync or delayed, it could be something else causing it. I have not seen any calls come in with your issues yet and I take a fair amount of calls for New Outlook.
Are all the users in one Office or hybrid/remote?
What AV are you using?
Firewall?
VPN?
These are the top 3 things I look at when there are calls regarding synch/delays in general, Outlook Classic esp if everything is configured correctly. AV is more common than firewall and VPN is causing a lot of Outlook issues, so much I tell my clients to get off it unless they need it. I have tested this a few times and the clients agree. The VPN would need to be configured differently, I don't do that so I don't know.
I'll watch this post and see what you reply, then I can maybe dig in further once I know what you say.
ok, just to let you know we investigated this and found when using network tools (netstat) we could not see any connections to the gmail servers. WHich was unusual, we also analysed the log files with the help of copilot and found a few entried regarding dropped push notifications. BUT no entries about gmail servers or imap and smtp ports. again, we found this strange. So when adding the account so we can use procmon I then read the below carefully.
the new outlook, when connecting using gmail address it does not directly connect to the servers. after reading https://support.microsoft.com/en-gb/office/sync-your-account-in-outlook-to-the-microsoft-cloud-985f9e19-d308-4e85-9d1d-0c6f32f8e981
... we then realised new outlook is not a traditional email client for imap. it stores and synchs info to microsoft servers. so it acts as a middle man. Although they are saying its more streamlined like this, i can see why his can delay emails! I am reading more about this and we have seen many compliants about delays
Good find! Yes I knew about how New Outlook works but that didn't dawn on me. In 365, you can add a Gmail connector, so that might help speed it up.
there is no vpn or any other network secure access app (e.g MS global secure access). we looked at the device windows defender firewall logs and there are no blocked/dropped packets. we also reviewed the defender online portal to see any reports of web filtering blocking. Nothing in event log either.
what we are going to do is analyse the corporate office firewall logs to see if there are any drops.
As I am just rolling the new outlook to particular tenants, I am only getting issues with users with google workspace emails. pure office 365 tenants are fine.
when I get access to those devices, I will analyse the event logs more, and use procmon and regmon to review as well as running the ms support assistant tool. I need to try and see where i can get the new outlook logs and setup entries so i can see what server its trying to connect to and see if there are any issues.
do you know where the logs are kept?
If you're asking about Outlook (new) logs, I have found them in the User AppData folder specifically C:\Users\USERNAME\AppData\Local\Microsoft\Olk
There's a Logs folder in that path.
Just recently we've had delays with certain users as well using Outlook (new) with Google Workspace users.Google fixed the last major problem with GWSMO and Outlook Classic with GWSMO ver 4.3.77.0. We have been rolling with that fine since June 2025 but for the last few days all of sudden we're unable to setup new Outlook profiles using GWSMO with Outlook x64.
It's happening with Windows 10 and 11. I have tried repairing Office, reinstalling GWSMO, updating Chrome, rebooting, all the usual suspects but no love.
The only fix for us (so far) is to uninstall Office x64, reboot, and install Office x86 along with the GWSMO 32-bit version.
