A method and system for customizing e-mail transmissions based on content detection determines when an e-mail user likely intends to customize an e-mail message and prompts the user to customize the e-mail message if they have not done so. A parser parses the e-mail message (including the subject line) for clues that indicate that the sender likely intends to customize the message in a particular manner, then the e-mail program prompts the user to perform the customization. The prompt may be generated in response to the e-mail program detecting that customization settings have not been entered or may be generated unconditionally upon detecting a clue. The parser may also decompose sentences to provide matching of common phrases or meanings with phrases or meanings that indicate that the sender likely intends to perform a particular customization. The e-mail program may further "jump" to the appropriate input area for the customization in response to detecting an associated clue or the e-mail program may skip on or both of jumping and prompting in certain cases.