Make Outlook prompt me asking if it should reduce attachments?

[kspezowka]

I recently reinstalled Outlook and found I had lost a very useful function:
Outlook used to prompt me when I was sending emails with attached photos,
asking if I wished to have it automatically reduce their size. I cannot find
this specifically in Help anywhere and am very frustrated! Yes, I can reduce
the files individually, but it was very helpful to have Outlook do several
all at once. V. grateful for any assistance!

 

[Noel All]

This doesn't sound like a vanilla install of Outlook that was doing this, I
think you had installed an addin that was giving that prompt.

 

[Brian Tillman]

I recently reinstalled Outlook and found I had lost a very useful
function: Outlook used to prompt me when I was sending emails with
attached photos, asking if I wished to have it automatically reduce
their size. I cannot find this specifically in Help anywhere and am
very frustrated! Yes, I can reduce the files individually, but it was
very helpful to have Outlook do several all at once. V. grateful for
any assistance!

Using the Outlook editor, click New to start a new message. Make sure the
format of the message is Plain Text or HTML. Click the paperclip icon and
browse to some picture. Select it and click Insert. The picture will be
inserted in the Attachment field and an "Attachment Options" button should
appear to the right of that field. Click that button and, at the bottom,
put a check in ":Show when attaching files". You can now dismiss the
Attachment Options pane and close the compose window. The next time you
attach something, the Attachment Options pane will reappear and allow you to
resize the attachment if it's a picture.