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Outlook in Office 365 constantly trying to upload 90MB files which fail

I have a client we have recently migrated to Office 365 (Exchange Plan 1).

One of the clients has some older mail in their Inbox which has between 30 to 90MB attachments each (that they have managed to send to each other internally - the old exchange was 2003) - Outlook is continuously trying to send these emails to Office 365 which fails as the message is too big.

Haven't an issue with that and my understanding is that this would just remain in the local Inbox and wouldn't be synchronised, yet all I see is constant re-transmission of the same email over and over again - which also means that the Inbox takes forever to update.

Is this expected behaviour or is something amiss going on as it is making the whole experience of cloud office 365 untenable for the customer as they cannot use Outlook.
I suspect that out of all of the 10 clients they all have the same issue to a greater or lesser extent.
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foxpc123
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foxpc123
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
There's no such thing as a "local inbox" for Office 365.

A user's mailbox in Outlook is a portion of their total mailbox stored online (only contains the last 12 months of messages by default -- the rest are online and accessed as needed).

But I don't quite understand what you are describing anyhow.  Why would a message in the INBOX be trying to transmit?  

Were the entire mailboxes migrated up to Office365?  If so, then did you use NEW Outlook Profiles for each user?

Jeff
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foxpc123Author Commented:
The office 365 accounts were created as normal. Then each Outlook client was then joined to the office 365 accounts.

Once this was established, then the old emails were imported into that Outlook client so that each client can see their new emails. Then can also view their old emails locally, and then over time these synchronise with the office 365 account, so that both the local account and server account match.

So until these synchronise fully, then essentially you have a local account and a server account with different amount of emails in each. So in reality there is a local and server account.

The issue here is that the imported email has emails which are greater than 20MB, some are up to 90MB in size, and so you can observe that the local account is trying to upload the email to the 'server' account and fails as the emails are too large, The problem appears to be that the outlook client repeats the attempt to synchronise over and over again, and so in time the local ost file just gets larger and larger with each failed attempt.

I have observed this increase from 15GB to 35GB over a period of a couple of weeks.

Perhaps this is an issue with regards to the methodology used, I'd be interested in a different method for clients with a small number of mailboxes, typically pop accounts etc.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
If all the messages were in a .pst file before migration, then you are right, importing through Outlook is the preferred method.

However, part of being prepared is knowing the parameters of Office 365.

Messages, including attachments, cannot exceed 25MB.  So what you will need to do for each user is this:

1.  Open the .pst file in Outlook
2.  Search for all messages which are larger than 25MB using this as the context:
 messagesize:>25 MB  
3.  Select all the messages found in the search and move them to a new .pst file

Things will then be working as you expect.
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