Changing Emails Bug in New Outlook Update 2026

Question

I was forced into changing my Outlook desktop app to 'New Outlook' after months of resisting because it seems there are always bugs - I was correct! Our IT dept can't even figure this one out and says it looks like a bug with the new Microsoft and Windows updates.

I have multiple emails I am managing on my outlook desktop app, and sometimes I need to change the 'sent from' email. First issue is instead of just changing the sender email, it opens a completely new email window and does not bring over any of my typed information. The larger issue is it will not carry over attachments of any kind, including Xcel docs which just seems silly honestly.

Anyone else experiencing this and/or have a fix to this issue?

Answer 1

Hi @Carly S, 

Thank you very much for reaching out and for sharing the detailed context. I appreciate your patience and the details you provided. Also, I'm sorry for the inconvenience this behavior in New Outlook may has caused to your workflow. 

A - What is happening 

In New Outlook for Windows, when you change the “From” address while composing an email, the app may open a completely new draft window under the newly selected account. Since this is treated as a new composition, the typed content and file attachments from the original draft do not carry over. Some users managing multiple mailboxes have reported the same experience. 

B - Recommended workarounds  

Here are my recommendations, which I hope will be helpful to you.

Please follow the steps below: 

1/ Start composing from the correct account 

Before selecting New Email, open the Inbox of the account you intend to send from. New Outlook will use that account as the default sender, helping you avoid switching the “From” field mid‑draft.  

2/ If you must change “From” while composing 

In the From menu, choose “Other email address…” and then select the desired address. Some users report this method may keep the existing content, though results can vary depending on environment. 

3/ Attach files after finalizing the “From” address 

Choose the sending account > (if needed) switch “From” > then attach files. Also note: attachment display differs between HTML and Plain Text, which can sometimes cause confusion about where attachments appear. 

4/ Optionally enable “Pop‑out to a new window” by default 

Go to Settings > Mail > Compose and reply > Pop‑out to a new window.  While this doesn’t change the “From” behavior, it makes copying/pasting content between drafts easier if needed. 

C - Submit feedback directly to Microsoft 

As a forum moderator, I hope you understand that I don’t have the ability to modify or escalate product issues directly. However, I strongly recommend submitting your feedback through the Outlook (new) · Community. This is the most effective way to ensure your voice reaches the product team and can be considered for future improvements.  

Once you've submitted your feedback, feel free to share the link here in the comments. I’ll be happy to upvote it to help bring more visibility.   

If you are unable to submit feedback from your side, please let me know and I will be happy to submit it on your behalf.      

Additionally, since many other users have expressed similar concerns but may not know where to submit feedback, if my response has helped you better understand the situation and guided you toward a possible next step, please mark it as the "Accepted Answer". Your action will help pin this post to the top, making it easier for others in the community who are experiencing the same issue to find your feedback and support it.    

Thank you again for your time and for raising this important usability concern. 

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