Jira Service Desk Cloud - Unable to setup Email Requests with Office 365 Kiosk account

Question

I am trying to get Service Desk Cloud to connect to a Kiosk account that I created in our Office 365. (I have even tried converting the account over to a E3 license)

I have tried setting it up as a Microsoft email and manually with SMTPS. Neither work giving me the same error message.

Your connection was unsuccessful

Unfortunately JIRA couldn't connect to the mail server. Here is what the mail server said:

"AUTHENTICATE failed"

I have reset the password, and testing logging in using the credentials with no problems so I know it is not a wrong username or password.

Has anyone ran into this issue and found a way to get it working with their Office 365 account?

Noah Hofmann_fybfec · Answer

I have the same problem. I've tried it with G Suite while creating an app password (because of 2FA) and moving my account to an organizational unit, which has imap still activated. After I was unable to set it up I tried my old Office365 account (no 2FA) and I got the same error.

In neither case I've received a warning email or anything.

--

Edit: It was due to not activated "Less Secure Apps" in G Suite.

Petter Gonçalves · Answer

Hello @Adam Horton

Thank you for reaching out.

Per your description, I understand you are trying to add a custom inbound e-mail address to receive tickets through e-mail in one of your Service Desk projects under project settings > E-mail requests. Is that correct?

Since you have double-checked that the e-mail account you configured is working and the password is correct, the most common reason that causes the authentication error is that your E-mail provider is blocking the Jira Service Desk application to access your account due to a specific requirement from your e-mail domain.

In fact, you may have even received an e-mail notification similar to the one below (This one is for Gmail) with a warning about the login attempt from Jira Service desk app:

That being said, check the following with your e-mail domain admins:

1 - Confirm if your account is not configured with two-step authentication

2 - Check if there are any restrictions from Apps not using the Oauth authentication methods

3 - Check if there are no redirections from the e-mail login page

4 - Check if your e-mail can be accessed from out of your network or VPN.

Additionally, check the tips in the thread below to further investigate all the possible blocks that your e-mail provider could be applying:

Unable to connect to Gmail (Google Apps) for custom email address in Service Desk

Let us know if you have any questions.