Emailing a jpg or pdf file as an attachment

Question

I have been emailed both a jpg and pdf file that I want to send attached to an email. The email box pops up with the file in the attachment box, then it won't send.

Answer 1

Have you upgraded to Yosemite?  Then you could send the attachment using Mail Drop.
You can use Mail Drop to send files that exceed the maximum size allowed by the provider of your email account. Mail Drop uploads the large attachments to iCloud, where they’re encrypted and stored for up to 30 days.
If you have an iCloud account and you’re signed in to iCloud when you click Send, Mail automatically sends the attachments using Mail Drop. Mail Drop attachments don’t count against your iCloud storage.
If you don’t have an iCloud account, or if you’re not signed in, Mail asks you whether to use Mail Drop (select “Don’t ask again for this account” to always use Mail Drop).
If a recipient uses Mail in OS X Yosemite, the attachments are automatically downloaded and included in your message just like any other attachment. For other recipients, your message includes links for downloading the attachments and their expiration date.
You can turn Mail Drop on or off for an account. Choose Mail > Preferences, click Accounts, select your account, click Advanced, then select or deselect “Send large attachments with Mail Drop.”