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Email attachments not showing up in Service desk

We have been using Jira Service Desk for a few months now, and just noticed that email attachments are not attaching to the tickets on replies anymore. The initial email will generate the ticket and attach whatever attachment it has to the ticket, but future replies will not attach documents. 

1 answer

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Hi Robert,

Just for us to better understand and help you with this issue, I'll make some questions:

When did this issue start? Was there any change on your instance?
Are you using a custom email address or the email auto-generated by Jira?
Are you using forwarding rule on your email to forward the customers' email to
Is it showing any other type of document attached to the ticket, .dat files, for example?
Do the images have the same name?

Best regards,

Hi Angelica,

It started a few weeks ago. There were no changes we made to our cloud instance.

We are using the email auto-generated by Jira.

We are not forwarding the emails, they are simply replying to the Jira notice that a tech has made a comment on their case and including additional information.

We do end up with winmail.dat files attached, but I have tried changing my replies to Plain text only with an attachment and have the same issue, same with webmail.

They are attaching documents with varied names. The winmail.dat files are all named the same and 0kb, and attach to the case.

Initial email does work correctly, so I do not know why the reply process is changing it on Jira's side.

Hi Robert,

This issue is related to malformed attachments from a Microsoft mail client, so this configuration must be done on the customers' mail client.
Probably if you convert the winmail.dat file on this URL, you will see what the customer sent.

Here are some links that you can send to your customers:


Why do some E-Mail attachments get converted into a .dat file?

How to Prevent Winmail.dat Attachments from Being Sent in Outlook

Related to this, we also have a feature request for Jira mail handler to understand and decode the winmail.dat to attach the file correctly on tickets:


For now, the only solution is to ask the customer to check outlook and make the configuration to prevent the files to be sent as winmail.dat.

If you have any other question, please let us know.


I've tested these solutions and this is happening across all of my users, including tests I do myself. This began suddenly and only happens when replying to emails from Jira notices. Are those notices sending as RTF?

Hi Robert,

If an agent attaches something directly to the ticket, the customer will receive the notification correctly. Jira does not convert the attachments into winmail.dat, this is something on the mail client side.
A test that you can make is to send an attachment using Gmail, for example, you will see that it will work.
Unfortunately, there is no workaround since this issue is that outlook converts the attachments once the email is sent.


Let me lay this out differently.

1. customer emails jira helpdesk email with attachment, case is created correctly and has attachment.

2. agent asks for second screenshot or updated file.

3. customer replies to this jira request with attachment.

4. attachment that shows up is 0.0kb winmail.dat.

5. if customer emails jira helpdesk directly and not through reply, new case is created with appropriate attachment. 


This is why I believe it is not our email doing it.

Hi Robert,

Can you please follow the steps provided on the documentation below to configure your outlook?

This indeed is something on outlook side, because if you answer a notification using another mail client, like Thunderbird, it will not happen.
Also, if you open a ticket using a Gmail test account and reply attaching a file using Gmail it will not happen.


I have done all of these configurations but still get winmail.dat in email replies, but not on original emails still. 

Hi Robert,

Whenever Jira receives an email with winmail.dat attachment is because the customer is sending the message/reply using outlook. It's possible to turn this off, but it must be done from Outlook/Exchange configuration and not Jira.
Please, check the steps on the documentation below:


Also, check this post on Microsoft community:



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