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I have around 100 files and can only send through Gmail (Dropbox is not an option in this case). Since Gmail and the destination Exchange server both have a file size limitation, I only want to send one file in each email.

Is there a tool that can batch sending files via Gmail?

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Are some of the files larger than the file size limitation? – Rook Nov 3 '11 at 1:14
Nope, I have already filter out oversized files. If there is any tool that can handle oversized tool, like zipping into several zip files would be even better. – Stan Nov 3 '11 at 9:26
you will need to write some program. In .net it would be fairly simple to send email, and filter and try to sort out larger files. – ppumkin Jan 18 '12 at 23:39

First of all note that GMail provides a standard SMTP server that you can use. Then you just need something that can send emails from the command line over SMTP with attachments. Without having tested it, I think smtp-cli could fit the bill nicely.

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