Q: iPhoto states server did not reply so I cannot email photos from iPhoto

Do you have two-step verification enabled  and are trying to mail from your iCloud account?

Then check this solution:

If you had two-step verification enabled, you have to set up an app-specific password for iPhoto, if you want to use iPhoto as a Mail client.

See the post below:

Re: I am using iPhoto version 9.6 and I can no longer get an email sent with a photo attached. I get an error message saying the email did not go through because the server did not reply. I can send the photo with Mail. Help!in response to Gary Kissler

This solution is for those of you using 2-step verification for your Apple ID and are using iCloud as the mail server that you are trying to mail photos with.

 

I too had this issue. The problem in my case occurred because I had setup 2-step authentication for my Apple ID. If you have done this then you will get the error message "the mail server did not recognize your email/password...". To solve the problem go to:

 

https://appleid.apple.com

 

• Click "Manage Your Apple ID"
• Verify your identity with the device you selected (if this step does not show up then you have not likely set up 2-step authentication and this is not your solution)
• Click Password and Security in the left column
• Click Generate an app-specific password
• Enter iPhoto as the name of the app
• Copy the password and paste this into the password box in iPhoto where you would normally enter your apple ID (in the mail account section in iPhoto preferences).

 

And...voila' (I hope)

Re: I am having trouble e-mailing from iPhoto the message I get is E-mail server didn't recognise your username/password combination