What will i do if my emails are being separated into new threads?

Hi. I'm Brian and I'll try to help.

By design, when you reply your message will not include any attachments that were on the original message? Why send back the same file when the sender obviously has it already or they wouldn't have been able to send it to you?

There might be some underlying issues to this, Jimmy.

What we can do at this point is take some test steps, observe and let’s try to spot this cause issue. The more steps you can carry out and provide clearer information the easier we will be able to spot what the issue is.

Observe Attachment Behavior

1. First off, at what point did you start having this issue? Were there any changes, settings made to your Outlook?
2. let’s recheck if the original email you're replying to, or forwarding does contain attachments. Is the attachment extension compatible with Outlook file formats? Is the size exceeding the attachment size?
3. Is this issue consistent with all attachment? Have you tried other attachments see how they behave?
4. Try sending, receiving, and replying to the same attachment using a different email service to check if the attachment is intact or affected.
5. Are attachments missing only when you reply to specific emails, or is it a consistent problem with all emails?

Observe Your Outlook Account Behavior

1. Does this happen to a specific email or all the emails in your account?
2. Use a different outlook account and test with the same attachment. Observe the behavior, see if the attachment is stripped when you reply.
3. Could you confirm if your email account has not reached its storage limit.
4. Do you experience this issue both on Client and the Web?
5. Try temporarily disabling any third-party add-ins, restart client and observe. Are there any spam and filtering rules? Probably they are unintentionally removing this attachment. Can you see the attachment in your spam/junk folder?

We will be able to work with any information you could provide.

There is still no attachement included on my replies