If you work in an environment that requires you to send a lot of emails everyday, someday you may just forget to attach a file that you’re supposed to attach to the email. That is just normal because most people just continue typing and only add the attachment at the end before sending out the email. If you immediately realized it, you can just resend another email with the attachment but if it was your last email before you leave your work desk, then the recipient will have just have to notify you that the attachment is missing and wait for you to send another email with the attachment. It can be a waste of time and sometimes embarrassing as it shows how careless or forgetful you are.
Gmail has an automated detection of certain keywords in the email body and alerts you if you’ve forgotten to attach files when the email doesn’t have an attachment. In fact Gmail had this feature for nearly 5 years already and today I’ve just found out that this feature is implemented in Hotmail as well.
Here are some keywords that I found to be in the list of keywords, there may be more so feel free to share in the comment area. You can try it yourself by composing a new email with any of the keywords below in the email body and send.
Hotmail:
see attached see attachment in attachment in attached
Gmail:
see attached see attachment
For Hotmail, you will get a popup saying “Send without attachments? Just checking. It looks like you mentioned attachments but didn’t add any“. There is a checkbox to disable this option but you can toggle it by going to Options and click on Sent message confirmations under Writing email. You will see an option for forgotten attachment reminders where you can select to check messages for forgotten attachments before sending or send mail without checking for forgotten attachments.

For Gmail, the popup message says “Did you mean to attach files? You wrote “see attached” in your message, but there are no files attached. Send anyway?“. I couldn’t seem to find an option to disable the forgotten attachment detector feature in Gmail.

The forgotten attachment reminder in Gmail and Hotmail is smart enough to only detect the keywords on the latest email conversation and ignores the previous conversation. Definitely a great feature!