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Connect Jira service management to IMAPS e-mailserver

Kees-Jan Lammers

Hi,

I'm trying to connect JIRA service management to an inbox using IMAPS. Whenever i try to connect (through project settings -> e-mail requests, using the correct credentials) i get the following error:

Received fatal alert: handshake_failure

If i try to set up an e-mailserver it seems to work. Trying to test the configuration of an e-mailhandler however gives this error:

javax.mail.MessagingException: Received fatal alert: handshake_failure while connecting to host 'blabla' as user 'servicedesk@yadayada.com' via protocol 'imaps, caused by: javax.net.ssl.SSLHandshakeException: Received fatal alert: handshake_failure

Usually i would add the ssl certificate to the java keystore and try again. Problem is, we use JIRA service management as SaaS, so i don't think we have access to this java keystore.

Does anyone have any ideas on how to fix this?

Kind regards,

Accepted answers

Charlie Misonne

Hi Kees-Jan,

I'm afraid you can't connect to a service using a self-signed or in-company CA certificate in Atlassian Cloud.

This can be read on Configuring Jira applications to receive email from a POP or IMAP mail server.

2021-06-28 14_51_34-Configuring Jira applications to receive email from a POP or IMAP mail server _ .png

Are you able to replace your mail server's certificate signed by a public CA?

All comments

Charlie Misonne

Hi Kees-Jan,

I'm afraid you can't connect to a service using a self-signed or in-company CA certificate in Atlassian Cloud.

This can be read on Configuring Jira applications to receive email from a POP or IMAP mail server.

2021-06-28 14_51_34-Configuring Jira applications to receive email from a POP or IMAP mail server _ .png

Are you able to replace your mail server's certificate signed by a public CA?

Kees-Jan Lammers

Hi Charlie,

Thanks for checking out this problem and replying. I did overlook this particular potential issue. However, i double checked and i'm not using a self signed certificate/in-company CA certificate, so i guess this shouldn't be a problem

Do you have any other ideas?

Kind regards,

Kees-Jan

Charlie Misonne

Well that's odd.

Do you use an on premise / self managed email server? Perhaps something is wrong with its key chain? A missing intermediate certificate for example.

To identify those types of issues I often the openssl command like:

openssl s_client -connect <hostname>:<port>

You can find similar websites on the we doing those checks for you. Example: www.sslshopper.com but I'm not sure whether it supports custom ports.

Or if you are using a SaaS mail solution like Office 365, Gmail, Hotmail, this is out of your league and I would suggest contacting Atlassian Support instead.

Matthijs Laan

The certificate is signed by Sectigo:

$ openssl s_client -connect <hostname>:443
CONNECTED(00000003)
depth=2 C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN = USERTrust RSA Certification Authority
verify return:1
depth=1 C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = Sectigo RSA Domain Validation Secure Server CA
verify return:1
depth=0 CN = <hostname>
verify return:1
---
Certificate chain
0 s:CN = <hostname>
i:C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = Sectigo RSA Domain Validation Secure Server CA
1 s:C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = Sectigo RSA Domain Validation Secure Server CA
i:C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN = USERTrust RSA Certification Authority
---

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