T 5.103 Misuse of webmail

If user information is not sufficiently verified, attackers can obtain e-mail addresses containing another person's name and undermine that user's reputation by sending spam mail or obscene messages under that name. If a provider allows its customers to choose e-mail addresses freely, an attacker can select an address with which other users make particular associations and use that address to encourage users to act carelessly.

With many webmail providers, the mailbox access username is the same as or derived from the e-mail address. If the password has not been selected carefully enough, or if any number of incorrect password entries are possible, an attacker can find out the password through trial and error and gain full access to the user's account.

Inappropriate user-friendliness often makes it easy for potential attackers to obtain a password and therefore gain full access to someone else's mailbox. A typical example is a mail provider whose start page already contains a "Forgotten your password?" link, which opens a page that prompts the user to provide previously agreed, often easily guessable information. Popular in this case is the date of birth, which, if entered almost correctly, may even prompt with further advice, like "Incorrect month".

Examples:

Following a virus warning, it can take several hours before the publisher of the virus protection program can provide the first effective updates and these updates are deployed across all IT systems. E-mails arriving on the mail server during that time can be quarantined. If safeguards are not in place to prevent e-mails being received through webmail accounts, PCs and servers in the LAN can be infected through this route.

Example: