Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello JanaStratton,
Based on your description, I did the same test on my side. In a new email, I attach a picture as an attachment and then click File, the option is available like the following picture:
Regarding to your problem, please double confirm whether the picture is added as an attachment before you click File. If you cannot see it, you can try uninstalling it and redownload it again to see the result. For more information about resizing picture attachment, please see: Reduce the size of pictures and attachments in Outlook email messages.
As a temporary workaround, you can directly insert the picture into your email message and resize it.
If the suggestion cannot work, to further assist you, please provide the following information to me:
1. The screenshot when you click the File.
2. The screenshot about your Outlook version. To get it, please click File > Office Account, in Product Information section, you can see the version about Outlook like the following screenshot:
Thanks for your time.
Regards,
Seven