Relevant documents can be attached to your issue by attaching the files while you creating an issue or after the issue has been registered.
Attaching files while creating an issue
While creating an issue, you can attach the documents by drag & drop the files to the attachment box or select files from your folder.
After you have added the issue, the attachment will reflect on the issue page under “Attachment” tab. Members can download or view the attachment, or you can manage and delete the attachment through there.
Attaching files after issue created
Tip💡: After an issue has been registered, by editing issue, there is no attachment function through this step.
How to attach a file then?
You can go to “…” icon just beside “Edit” icon, and select “Attach File”.
Attachment box window will pop-up and you can start to attach relevant files. Thereafter, the attachment will reflect at the comment section and click on “Submit”, the files will attach within the issue.
File size & limitations
The number of attachments per issue and file size per attachment is limited, depending on your plan. Here are the summary details:
Happy Weekend! 
So now i know why couldn’t email issues with multiple attachments! It would be useful if this information was given in the error message (or perhaps in your pricing grid) - ie it is because of the plan, nothing more 
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Attachments that have been added to a comment in this fashion seem to disappear if the comment is not submitted (still being edited and previewed) after a number of hours. Just the attachments. My typing for the comment is still intact.
Ok so submit it promptly! But I suffer from this shortcoming because I have a habit of editing and preparing my posts maybe in the evening and submitting it many hours later during the business hours next day. I don’t want to alert my colleagues at night.
Can someone look into it please.
Thanks!
Tatsuo
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@tatsuonatsukawa Thank you for your feedback.
This is a use case (writing a comment and submitting it later) that’s new to me! 
Thanks for sharing.
I’ve forwarded it to our Backlog team.
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@tatsuonatsukawa
When writing a comment, Backlog only stores the draft text in your browser locally, but attached files/images are not stored.
If the draft comment is left for hours or overnight, when the computer goes into Sleep/Hibernation and then reawakens, the webpage will reload… Hence, only the text and image tags are restored but any previously attached files/images are not.
You will have to drag and drop them in again; sorry for the inconvenience. 
This isn’t a function that Backlog provides at the moment, but I’ve passed your feedback to the team for consideration in the future roadmap.
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