Hey @jyau and @srivera,
This is a known issue that our engineering team is working on. There are some workarounds you may be interested in; on this Microsoft article we have had success with options 2 and 3. For option 3, I recommend following these instructions (you'll need to be an admin on your Office365 account):
- Once logged into Office 365, click the Admin app
- From the navbar on the left scroll down to ADMIN, then click Exchange.
- From the navbar on the left click Mail Flow
- Click the Connector tab (on the right)
- Click the plus button
- In the "From:" field select "Your organization's email server", in "To:" select "Office 365". Click Next
- Enter a name and a description. These can be anything you like. Make sure "Turn it on" and "Retain internal Exchange email headers" are checked. Click Next.
- For "How should Office 365 identify email from your email server?" select the "By verifying that the IP address of the sending server matches one of these addresses that belong to your organization".
- Click the plus button and enter the IP address or range that Looker will be sending email from. Click Next.
- Click Save.
For step 9, if you are hosted by Looker you can find the range of IP addresses that we use on this page.
Once you've gone through the instructions above to set things up in Office 365 the next step is to set up Looker's SMTP page. You'll want to use custom SMTP and the only thing to note is that you leave the username and password blank.