On 23 September 2005 the company announced plans to phase out the character, and on 27 February 2006 Jeeves was disassociated with Ask.com. A competition was run on Ask for Kids as to what Jeeves should do when he retires. The winner was World Cruises.

The original idea behind Ask.com was the ability to answer questions posed in natural language. Ask.com was the first commercial question-answering search engine for the World Wide Web. It supports a variety of user queries in plain English (natural language), as well as traditional keyword searching and strives to be more intuitive and user-friendly than other search engines. Ask Jeeves sold the same technology used on the ask.com site to corporations including Dell, Toshiba, and E*Trade. That part of the business was sold to Kanisa in 2002.

Ask.com-owned Teoma search technology uses subject-specific link popularity to compute "authoritativeness" of a search result. The Teoma technology also incorporates patented click popularity techniques, originally from the DirectHit search engine, which Ask Jeeves acquired in 2000. On 26 February 2006 Teoma was rebranded and redirected to Ask.com.

Ask.com stock traded on NASDAQ stock exchange from July 1999 to July 2005, under the ticker symbol ASKJ. At the time of the IPO in 1999, ASKJ had the 3rd best first-day performance in history. In 2003, it was the 51st best performing stock out of 3229 companies on the NASDAQ. The price of Ask.com stock soared more than 500% throughout the course of the year. In July 2005, ASKJ ticker was retired upon the closing of the acquisition by IAC/InterActiveCorp. IAC/InterActiveCorp trades on NASDAQ under the ticker symbol IACI. The IAC/InterActiveCorp deal was announced in March 2005 valuing ASKJ at $1.85 billion. IAC/InterActiveCorp is a media holding company founded and run by Barry Diller.