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Unable to connect to Gmail for custom email address in Service Desk Project

I keep getting the error "Unfortunately JIRA couldn't connect to the mail server. Here is what the mail server said: "[AUTHENTICATIONFAILED] Invalid credentials (Failure)" Check out our troubleshooting docs for help resolving the issue." despite following all the instructions and making their changes to the email account and yet it still fails

Before anyone advises that I'm entering the wrong details I can 100% assure you that I am as when I don't enter the app specific password I get this error "Unfortunately JIRA couldn't connect to the mail server. Here is what the mail server said: "[ALERT] Application-specific password required: (Failure)" Check out our troubleshooting docs for help resolving the issue."

So I know that JIRA and the Gmail account are talking but despite deletion of the app specific password and recreating it. As well as enabling less secure apps to work with the account and ensured that I approved it I still can not get JIRA and the Gmail address to connect for the project incoming email address.

I have seen the question that has previously been raised for this issue and unfortunately I can not see how the issue was resolved and require some assistance to fix this problem please


7 answers

Just got it to work for G suite do the following:

  1. Turn less secure apps on
  2. Turn 2 step verification on
  3. Create app password
  4. Login with email address and app password

This is the solution :) 

Worked as a charm

Can you expand on this. Where do you go for step 3?

For G-Suite users - after you enable access to less-secure apps in the Admin console, you need to go to the specific Gmail account you are using, go to the Account Settings, and explicitly allow Less Secure Apps for that user. You also need to enable IMAP for that account.

For GSuite Users

1️⃣ Go to Google Account settings and enable less secure apps (

2️⃣  Enable IMAP in Gmail

Any body solved it , as my issue is the same;

I've seen a lot of questions in the forums on this, but how do I get Jira Service desk access to a Gsuite email account with 2FA enabled. (Relates to Connect to customer email account from a Email Requests for a specific Jira Service Desk project)

I have added App specific password as been mentioned in previous questions as a solution but then fails with authentication issues not that 2fa is on, also IMAP is on for the particular account.

First Step with normal Password;

Screenshot 2020-04-01 at 14.08.52.png

Second Step after creating a APP specific 16 length password

Screenshot 2020-04-01 at 14.09.02.png

To one particular on less secure apps, we can't enable less secure apps on our gsuite domain "Google is beginning to shut off Google Account access to less secure apps, the enforcement option is no longer available. We recommend turning off less secure apps access now. You should start using alternatives to less secure apps."

🤔 I didn't know about them shutting down less secure apps. Everything is okay with our service desk (so far).

Now I found some articles where google talks about this:


According to the second one, Less Secure Apps  should work until June.

I'm personally not aware of any alternatives, I think that Jira will have to implement OAuth for Gsuite, but I might be wrong.


As I tried switching on less secure apps for first time on our gsuite , it wouldnt let me so its not something we already had on.

Thanks for the links will look at them, and see if they help.

Just got it to work for Gsuite do the following:

  1. Turn less secure apps on
  2. Turn 2 step verfication on
  3. Create app password
  4. Login with email address and app password
Like # people like this

Thanks @sfaria - Your method worked ... It was a bit of a runaround but worked ... Thank you.

Like spryce likes this

same issue

A support ticket has been created for this issue also JST-460515

Are there any follow ups on this? My team is having the same issue. 

The same is happening to us right now! 

Did you solve it ?

Ok for anyone finding this already almost a year later. For me, adding 2 step verification and then creating an app password worked.

I already approved less secure apps beforehand

worked perfectly!

which settings you have choosen. I will try after few hours ago, app password is not accepting in my side

App Passwords are not working for me either.


Atlassian, please implement OAUTH instead of app passwords.

I have same problem...still not working... 

Login the email box

  1. Manage your Google account
  2. Security
  3. go to section called "Signing in to Google"
  4. Setup 2 factor (once done go back to section called "Signing in to Google")
  5. Select Apps password
  6. Go to Atlassian and sign in with it (project setting --> email requests)

I do see issue when doing it with different browsers (chrome -- worked, internet explorer --failed, Firefox --worked) 

Like Tarcísio Bannwart likes this

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