Ozzie.eu

For the past days I’ve been bugged by a weird behavior on my professional organization software, Microsoft’s Outlook 2013. Apparently at random, it hanged when sending replies to e-mail messages.

After reading the manufacturer’s suggestions to solve the given scenario, I checked them all out (and if you have the same problem, you should too):

• This issue can occur if you have not installed the latest updates.
• Outlook may be in use by another process.
• A previously installed add-in may be interfering with Outlook.
• Your mailbox may be too large.
• You may need to repair your Office programs. 
• Outlook data files may have become corrupt, or damaged.
• Antivirus software may be outdated, or conflicting with Outlook.
• Your user profile may have become corrupt.
• Another program may be conflicting with Outlook.

After going through all of that unfruitful effort, I noticed that the program only crashed when replying to digitally signed messages. With that piece of information I arrived at this support article:

Application freezes when you access a password protected certificate in Windows 8

I requested the hotfix, downloaded it and restarted the PC. I took one of the messages that caused the crash and then, instead of crashing, the following window appears:



This is because I also have a digital certificate installed and Outlook tries to reply in the same fashion as the sender.

Hope this helps someone.

I switched my Hotmail account to outlook.com and the desktop Outlook stopped being able to fetch my messages, contacts and calendar stuff.
When you switch from a Hotmail or Windows Live address to a new outlook.com address your previous address becomes an alias.
Here's what you have to do on this forum thread: I switched from Hotmail to Outlook.com, why doesn’t Outlook Hotmail Connector work?