Mail app on iPhone - go in Settings, find Mail in the list, select Include Attachments with Replies in the Composing section and select ' Always:. Apple Mail on Mac - go to the Edit menu, go down to Attachments, then select Include Original Attachments in Reply:. If you want to use Mail app on Mac and iPhone and see the images in the signature of Outlook Windows user, follow the next steps: When you reply or forward an email, sometimes email signature images are missing and replaces with image tags at the recipient end: 
This is standard behavior for Mail App on all iOS devices (iPhones and iPads) and Apple Mail on Mac OSX.
When emails sent from Outlook on Wind ows (or Xink fully server-side with embedded images) and replied from Mail on iOS or Mail on OS X, the images are removed because images are embedded in the email and Apple email clients does not support embedded images which was developed by Microsoft and launched in Outlook 2007 version.
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