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Any number of attachments can be copied to the related issue/-s.

Configuration

Position of the Post Function

If you use 'Move Attachment' (see bellow) you must position the post function before 'Update change history for an issue and store the issue in the database.'

You can add this post function several times in one transition and it will duplicate attachments.

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Copy attachment from/to all issues related as

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Warning
titleConditional copying attachments

Conditional copying attachment (controlled by custom field) is checked always only for issue in transition.

Independently if issue in transition is a source or destination.

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(info) Tip: You might choose 'Move Attachments added during Transition'. The user then adds some attachments on the transition screen of the source issue. However since they are moved to all related issues, it feels as if he just added the attachments to all related issues. 

Position of the Post Function

If you use 'Move Attachment' (see bellow) you must position the post function before 'Update change history for an issue and store the issue in the database.'

You can add this post function several times in one transition and it will duplicate attachments.

This post function can be also used in a combination with preconditions.

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Info

If you use 'Move Attachments added during Transition' it is important that the 'Copy / Move Attachments' Post-Function is before JIRA Post-Function 'Update change history for an issue and store the issue in the database'!

Status
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titleException

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titleException from this rule is a situation when Transition issue is a destination issue

In such case "Copy Move Attachments" has to be placed between "Update change history for an issue and store the issue in the database" and "Re-index an issue to keep indexes in sync with the database"
Otherwise transition attachment will not be properly stored and it will be not attached to the current issue.


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