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Some e-mail randomly doesn't show up in a user's Outlook 2011 inbox. Could this be a Kerio Connect issue or is this a larger Outlook 2011 issue?

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You should try:
- upgrade Kerio Connect to latest version 7.3.1
- upgrade Outlook 2011 to latest version 14.1.4
- reindex user's mailbox
- check if these messages are visible in WebMail or another client

It it will not help, you should contact our Technical Support and send him example of such messages (.eml files from Kerio Connect store).
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