How can I attach multiple photos at once sending email through Gmail app? Alrighty, so I’m annoyed that whenever I want to attach images from my iPhone into an email on the Gmail app, it only lets me select one pic at a time. The solution seems to be instead to use a different email app.

Understanding the Context

At least using Outlook seems to work - and ONLY if you initiate sending the photos from the Photos app. If you start within Outlook and attach pictures, you end up with embedded pictures. Remains to be seen whether the same holds true if using other third-party email apps. I tried attach several files in a email reply, and it worked just what many of you wished a iPad could do.

Key Insights

Another nice thing is that you could open multiple email accounts at once or open multiple attached files at once in a browser like user interface. And it supports cloud, Wifi, Open in as well, so you could get files in and out easily. To use the "Attach" function, you would have to designate this new Library as the System Library in Settings>General. Don't turn on iCloud for this Library. Make a new user and see if the same problem recurs with it Rebuild your Photos Library--close Photos and re-launch by option-command-clicking the app icon.

Final Thoughts

How can I attach multiple photos at once … - Apple Community How do I attach a pic to a reply email? - Apple Community Mac Mail won't attach some files Suddenly my Mac won't attach files to emails. Not every file, some still work, but most. When I drag the icon of the file to attach it, it says "downloading" beneath it. (This is to attach a file to send it, not to download an incoming file).