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Microsoft Outlook had problems
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https://www.kaskus.co.id/thread/5b182452d44f9fed548b4567/microsoft-outlook-had-problems

Microsoft Outlook had problems


When I send an email with S/MIME encryption the error pops up, "Microsoft Outlook had problems encrypting this message". Why does Outlook give me this pop up every time? 
Beri apresiasi terhadap thread ini Gan!
That seems to suggest that Outlook cannot connect to a remote server. If that's the case and the network connection genuinely hasn't been lost then it may be that a repair/reinstall is the easiest option as determining the source of erroneous errors like this can be rather time-consuming. If that doesn;t work then I'm afraid I have no better suggestions.
For more Outlook recovery info https://www.repairtoolbox.com/outlookrepair.html


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