Using classic Outlook for Windows in educational settings
Dear @Eitan Caspi,
Thank you for posting your question in the Microsoft Q&A forum.
Based on your description, when saving or dragging emails to the file system as .msg files in Outlook Classic (Microsoft 365), Hebrew characters are converted into HTML numeric references and some words are duplicated, while the original email and HTML/MHT exports display correctly.
Since the original message renders correctly and the issue only occurs in the .msg file, the problem is related to how Outlook serializes message content into the MSG format rather than your encoding settings.
Currently, there is no confirmed permanent fix, but you can try some following suggestions:
Check and enforce encoding settings
Go to File > Options > Advanced Under International options: Uncheck Automatically select encoding for outgoing messages Set Preferred encoding to Unicode (UTF‑8) Restart Outlook and test again
(Note: This may not fully resolve the issue, but helps rule out misconfiguration)
Test in a clean profile
Create a new Outlook profile and reproduce the issue: Control panel > search Mail in search box > Click Show Profiles > Click Add… Enter a name for the new profile (e.g., TestProfile) > Click OK.
Then Enter your email address and follow the prompts to sign in > Complete the setup > Under When starting Microsoft Outlook, use this profile: Select Prompt for a profile to be used
Open Outlook again > Choose the new profile you created
This helps determine if the issue is profile-specific or a product bug.
Please also try to check the issue in Outlook on the web and New Outlook, so I can better understand where the issue is coming from.
Use alternative formats when possible
If you need correct character preservation, save emails as .HTML or .MHT This is the most reliable workaround at the moment
In case you have tried all the methods above, but the issue still persists. I recommend you should contact to Microsoft Support team. The Microsoft Online Support Team has higher permission than us moderators to remotely assist you and collect background logs for the root cause. This is a more efficient and direct way in recovering this scenario for you.
If you are user, you can contact to your IT/administrator of your school. They can follow these steps as the link: Get support - Microsoft 365 admin to help you submit support ticket.
And if you're unsure who your Global Admin is, this guide may help How do I find my Microsoft 365 admin? - Microsoft Support
If you are an Admin, you can use this link to find the appropriate contact number: Global Customer Service phone numbers - Microsoft Support
Or you can raise support ticket: https://admin.microsoft.com/#/support/requests In the Microsoft 365 Admin Center > Support > Help & Support.
Please feel free to reach out if you have any other questions.
Note: Please understand that as forum moderator, my primary goal is to provide helpful guidance and support through general troubleshooting steps. While I don’t have access to internal systems or test devices required to resolve backend issues, I truly appreciate your understanding of these limitations. I genuinely hope the information I share helps guide you in the right direction, and I'm always here to assist as much as I can within my scope.
If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.