Mac mail attachments not searchable in gmail webmail

Attachments sent for my Mountain Lion Mail.app (using my gmail account) are not searchable from the web gmail.com when I use advanced search options like "has:attachment".
However, emails with attachments sent from web gmail.com are searchable. For some reason gmail does not recognized the mac mail sent email attachments as attachments even though the paper clip is there.
For instance. I can search my sent folder, find the email and clearly see the attachment (and paper clip) are there. However if I do a search just as "to:[email protected] has:attachment" it only show emails that originated from web gmail.com
Any suggestions?

The correct settings for Gmail are posted below, verify that your settings match.
Incoming
Gmail IMAP server address: imap.gmail.com
Gmail IMAP user name: Your full Gmail address (e.g. [email protected])
Gmail IMAP password: Your Gmail password
Gmail IMAP port: 993
Gmail IMAP TLS/SSL required: yes
Outgoing
Gmail SMTP server address: smtp.gmail.com
Gmail SMTP user name: Your full Gmail address (e.g. [email protected])
Gmail SMTP password: Your Gmail password
Gmail SMTP port: 465
Gmail SMTP TLS/SSL required: yes

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Mac mail attachments not searchable in gmail webmail

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