Office365 SMTP setup


#1

Has anyone had success using Office 365 for SMTP with Looker?

I get this error when attempting to send a test email:
Failed to send mail: 504 5.7.4 Unrecognized authentication type

I’m selected the check box for SSL/TLS. I did note that the setting I’ve had to use with another tool is START TLS. I’m not clear on whether that variant should be handled by the SSL/TLS option.


(Sonny Rivera) #2

Did you ever get this answered and working? I’m looking to do the same thing.


#3

Nope. I haven’t tried since, but the options don’t look like they’ve changed much. We’ve been using the default email settings, which are less of an issue now that we’ve had our IT team add the address (and potentially some IPs, I don’t remember) to our global whitelist in 365.


(sam) #4

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):

  1. Once logged into Office 365, click the Admin app
  2. From the navbar on the left scroll down to ADMIN, then click Exchange.
  3. From the navbar on the left click Mail Flow
  4. Click the Connector tab (on the right)
  5. Click the plus button
  6. In the “From:” field select “Your organization’s email server”, in “To:” select “Office 365”. Click Next
  7. 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.
  8. 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”.
  9. Click the plus button and enter the IP address or range that Looker will be sending email from. Click Next.
  10. 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.


(Ian) #5

Hi,
has this been resolved yet? Our security team are not keen for this work around.


#6

Hey @IanT,

This is on our engineering team’s radar. If you’d like to provide further details of your use case or security team’s concerns feel free to email support@looker.com with those details!


(Ian) #7

Hi, I know/understand very little about this however security told me this:
“whitelisting some outside servers we have no idea how well they are managed to peer into our email tenant is not a great security practice”.
We will probably end up using the default server settings until TLS is implemented.
Thanks


#8

Hey @IanT,

Thanks for providing those details! I’ve passed them along to the team.


(Ian) #9

Hi,
Has there been any movement on this?
Thanks!


(Chris Sarakopoulos) #10

Hey @IanT I’ve asked the team again! There’s a discussion going on but we don’t have an ETA at the moment.


(Justin Johnson) #11

Any update on the internal discussion around improving this? Thanks.


(milli.koch) #12

Hi @balduncle,

The engineering team is still working on this. At the moment there isn’t a timeline for improvements but if you have any further context on your use case to provide please send that along to support@looker.com so we can add that to the discussion!