If Add2Exchange was working and now it's not, post here.
Deleting Alerted Relationships
For Add2Exchange: (For specific Add2Outlook instructions, see below but the conversation is similar. Read this entire post)
DON'T Delete alerted relationships if you are going to try to remake the relationship again. You can delete an alerted relationship if the user is gone, hidden from the GAL or the folder was deleted. If this is the case, you will need to set in the Console to Empty Trash.
If the user is there still, and the folder is in the deleted items, you can move it back to the original location and you can use the Recovery and Migration Tool called "Add2Exchange Recovery and Migration Manager or (RMM.exe) and repoint the relationship. If it is not in the trash, delete the older relationship and remake a new one.
If the user has changed their email address, such as getting married or a new domain, often this triggers the relationship can go into alert. Use the Recovery and Migration manager and pick the original user from the GAL. Be careful, you cannot pick ANOTHER user from the GAL and "Change" the relationship source or destination. If this is desired, then delete the original relationship and create a new one.
Be sure to download the latest versions of Add2Exchange and RMM from the website and uninstall the old and install the latest. DO NOT RUN older versions.
The RMM tool fixes alerted relationships. If an alerted relationship is deleted the destination is may be unavailable it will not be able to clean up the copies from the old relationship. Remaking the same relationship will create duplicates which will have to be removed with the Add2Exchange Toolkit and Surgeon General tool.
Use the Recovery and Migration tool to fix the relationships in Add2Exchange if possible. Download and use the appropriate tool, Recovery and Migration Manager Enterprise Edition from here: http://support.diditbetter.com/downloads.aspx
You almost always want to fix alerted relationships but sometimes can't because the mailbox has been deleted. Then you have to delete it and select to Empty Trash from the Global Options. If you are are planning to remake the same relationship from this or another Add2Exchange Installation, be careful not to intentionally create duplication. It is best never to delete an alerted relationship if you can fix it.
TIP: If during the Recovery process, the tool can not find the account, it could be possible the account is hidden from the GAL, so the resolution is to stop the tool, then unhide the affected account from the GAL and then run a full sync to have the system automatically get the relationship out of alert status. If it still does not, run the RMM tool again.
Download and run the Recovery and Migration Manager Tool to repoint to the folder and fix the relationship. Buy Now
See this tip on how to avoid duplication if you deleted an alerted relationship and you want to recreate it: http://support.diditbetter.com/Forums/Thread.aspx?thread=97&mid=2&pageid=1&ItemID=1&pagenumber=1#post209
Deleting Non alerted Relationships - Normal relationship deletion options
Try not to leaving the destination Items as Copies unless it is a Calendar item and you termed an employee and need to refer to the appointments for future convenience. I would not suggest doing that to all relationships, just the covering user. These items "static items" and will not update again. Do not use this option for Contacts or Tasks because it creates static "orphans" and it is sometimes hard to tell the syncing ones from the static ones.
If you don’t need them or want them, select to Remove destination items. We almost always suggest to remove destination items.
Again, almost always, if this is a Contact relationship, when deleting the relationship, select to Delete the Destination Items so as not to create “orphans”, or non-replicating copies in destination Contact folders. If you wish these items to replicate again, after this process and a full "desync" only the original items will be left in that users folder and you can manually open the users folder and take the originals from the original user's source folder and copy them to another source folder of an active relationship.
Add2Outlook has the Recovery Tool built into the Add2Outlook Console. The same conversation applies about deleting alerted relationships as mentioned above.
To fix an Add2Outlook Relationship, you can right click and select Recover it.
For non default folders, you can use powershell to disable ownership of that folder in client access permissions, so users cannot accidentally delete it.