To troubleshoot Outlook not properly syncing with third-party applications, please do the following:

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1. Check that your Outlook calendar is connected to the email associated with the third-party app.
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2. Check that bug fixes have been applied for Outlook and your third-party app.
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3. Make sure that the time and date settings are the same within Outlook and the given third-party app.
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4. Check that the version of Outlook (32-bit or 64-bit) is compatible with the third-party app.
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5. Disable antivirus software temporarily to test the app and Outlook interaction.
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6. Reinstall the latest version of Outlook.
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7. Contact your IT administrator to potentially reset the connection between Outlook and the third-party app.