LeakyCon was a series of fan conventions that occurred from 2009 through 2024 and were organised by Mischief Management, LLC. The frequency varied, but it was generally an annual convention.

The first event was held in Boston, Massachusetts, with an attendance of over 750. Attendance peaked in 2018 in Dallas, Texas, with 18,000. In 2024, a reported 2,800 people attended the final Portland, Oregon convention. It was held in a total of six cities within the United States, as well as London, England and outside Dublin, Ireland, with a total of sixteen conventions between 2009 and 2024.

Activities included live performances of wizard rock as well as fan-made productions, panels ranging from scholarly discussions to question and answer sessions with stars as well as both film and literary industry experts, live recordings of podcasts, Quidditch, and autograph sessions. Scholastic, Warner Bros., Sony Pictures, and Simon & Schuster chose to premiere new material to fans through LeakyCon over various convention years. In 2011 and 2014, LeakyCon attendees were able to purchase special "Open at the Close" tickets to enter The Wizarding World of Harry Potter in Orlando, Florida. Attendees in 2016 were able to purchase special tickets for the Hollywood theme park.

An attempt in 2015 to move LeakyCon away from the multi-fandom event it had become through renaming the main convention and holding a separate LeakyCon in 2016 as a smaller, intimate event to return to being solely a Harry Potter event was abandoned by 2017. Following the COVID-19 pandemic and postponement of both the 2020 and 2021 conventions, however, sales declined as some of the audience typically attending LeakyCon no longer felt comfortable doing so after J. K. Rowling's comments in support of transphobic feminism. Mischief Management CEO Melissa Anelli announced that the convention would broaden its base audience and distance itself from Harry Potter in 2023.

The decision was made to end LeakyCon with the 2024 Portland convention and establish a broader fantasy-centric event named EnchantiCon.

Overview The idea for LeakyCon originated from a convention The Leaky Cauldron web staff attended together in 2007.

Preliminary funding LeakyCon was directed by Melissa Anelli and Stephanie Dornhelm, both as volunteers for The Leaky Cauldron. They had originally intended to call it CauldronCon, but a convention by that name had already been held in Massachusetts in 2005.

Prior to the first LeakyCon in 2009, wizarding rock groups performed for a fundraising night outside of the Terminus 2008 convention in Chicago. The dance party, held on Friday, 8 August 2008 and only accessible by showing ID to prove the attendee was at least seventeen, was organised by Wrock Wreggies. Performers included The Chocolate Frogs, Dreary Inferi, Swish and Flick, and The Whomping Willows. Though separate from the Terminus conference, transportation was provided to the concert for Terminus ticket holders.

Even with the fundraiser, Anelli used of her own money to start LeakyCon, and had to borrow funds from her parents to pay for the initial convention.

Charity LeakyCon was promoted as a charity event, with the editor of LeakyNews stating, "Just by attending LeakyCon, people are giving back and helping those less fortunate."

The first convention's proceeds went to benefit Book Aid International and the Harry Potter Alliance. Later conventions added the This Star Won't Go Out foundation and Friends In Deed. The first convention raised for charity. LeakyCon 2011 brought the total to . 2012's Chicago convention raised the total to . By 2015, the total donated to charities exceeded .

Imagine Better, an initiative intended to spread the charitable efforts of the Harry Potter Alliance to other fandoms, was created at LeakyCon 2011 out of concern that the social awareness projects would end if the Harry Potter fandom were to become a "zombie fandom" after the release of Harry Potter and the Deathly Hallows – Part 2 on 15 July 2011.

In 2013, LeakyCon instituted a scholarship program, offering for academics. An art fellowship for was also available.

Composition Attendance consisted primarily of young females, and was supported by Nerdfighteria members. Cosplay was common and spanned multiple fandoms.

Many attendees were LGBTQIA+ people, some of whom preferred to identify with the abbreviation GSM. LeakyCon was "an intersection of largely female, queer-friendly youth cultures". According to Anelli in 2023, LeakyCon statistically had a ratio of genderqueer and gender non-conforming attendees that was at least five times greater than other comparable U.S. events. Issues important to this community, like marriage equality, were sometimes addressed in a whimsical manner at the convention, such as the Harry Potter Alliance holding a vote at LeakyCon for Harry Potter character marriages. Gender-neutral bathrooms were instituted at the rebranded GeekyCon in 2015, and continued to be a feature once the name reverted to LeakyCon, both before and after Rowling's anti-trans rhetoric.

Booths at the convention reflected attendees' social activism, featuring animal rights activists and organizations such as Uplift with a focus on sexual harassment. Such activism extended to activities at the convention, such as when attendees demonstrated their opinions of rape culture at the 2014 Esther Earl Ball. When the DJ began to play "Blurred Lines", the dancing stopped and everyone booed until the song was changed.

One criticism of the composition of attendees was the lack of outreach to non-white and marginalised communities, and specifically that fans in the city where the convention was ongoing in communities of color were entirely unaware of LeakyCon.

Content Regardless of its advertisement as a Harry Potter convention, LeakyCon attracted fans from multiple fandoms. Attendees were even fans of fanworks. For example, wizarding rock music was a staple at LeakyCon events, with significant parts of the conventions being dedicated to live performances. LeakyCon provided the largest audience at a single time for wizarding rock musicians in the United States. Attendees developed their own traditions around wizarding rock, such as "The Circle of Awesome", which had been in practice since 2009. Wizarding rock involvement was also a part of GeekyCon, and EnchantiCon 2025, which also had a wizarding rock concert held offsite, separate from the event itself.

Panels included discussions on civil liberties, the cultural impact of Harry Potter as a "phenomenon", its impact on literature, and social justice. Critique also extended to literary analysis and the question of objective consumption of the series. Some panels debated what material constitutes the canon of Harry Potter.

At some of the conventions, they broached controversial social issues, expanding the context of depictions in Harry Potter to the real world and allowing debate of issues such as civil rights, white privilege, and segregation. Panels also included critique of Harry Potter in relation to diversity, which extended to the representation of Korean history in relation to Fantastic Beasts: The Crimes of Grindelwald, specifically with respect to Nagini.

Panels at the 2022 Orlando convention addressed the Harry Potter LGBTQIA+ community's reactions to Rowling's gender identity comments.

Staffing LeakyCon was dependent upon volunteers: the 2011 convention included among its attendees more than 140 volunteers, and in 2012, Anelli recruited an unpaid social media manager. The entire staff of the 2012 convention were unpaid volunteers. In 2014, pop-up programming sometimes relied on attendees volunteering their time and talents.

Panelists were unpaid. In one particularly memorable panel at the 2012 convention, attendee and Severus Snape cosplayer Nigel Taylor ended up giving a lecture on Lily Evans when the scheduled speaker didn't show.

2009 The inaugural convention took place at the Park Plaza Hilton in Boston, 21–24 May 2009. There were more than 750 attendees and more than 70 various panels and activities. Among the invited guests were Michael Goldenberg; keynote speakers Hank Green and John Green; Lev Grossman, who was discussing his then-upcoming release of The Magicians; Arthur A. Levine Books senior editor Cheryl Klein; and Kansas State University professor of British literature Karin Westman.

Among the performers were the Potter Puppet Pals. Live music performances at the event were compiled onto an album which was presold online for and presold at the event for , with proceeds benefiting Book Aid International and the Harry Potter Alliance. Draco and the Malfoys, Gred and Forge, Harry and the Potters, Justin Finch-Fletchley and the Sugar Quills, The Moaning Myrtles, The Mudbloods, The Parselmouths, The Remus Lupins, Riddle TM, Swish and Flick, Tonks and the Aurors, and The Whomping Willows performed live, and all had recordings on the album. Music performances at the event were divided into three separate programs, not including performances that took place as a part of other portions of the convention. The groups The House of Black and Ministry of Magic also had recordings included on the album, which was released 25 October 2010.

An authenticity-certified signed hardback set of the Harry Potter novels and companion books, ten in all, was provided by J. K. Rowling specifically for LeakyCon in 2009; to obtain the set required attendance at the event.

2011 No LeakyCon took place in 2010, as The Leaky Cauldron crew who had organised the 2009 convention had planned to take the year off, though Anelli told Reuters that the interval between conventions was to allow attendees to be able to budget for the cost of traveling to Orlando. Rather than a year off, the LeakyCon crew were contacted by Hank and John Green and helped to organise the inaugural VidCon.

The 2011 convention was held 13–17 July 2011 at Loews Royal Pacific Resort in Orlando, Florida. There were 3,400 attendees, including over 140 volunteer staff. A private party for the convention took place inside The Wizarding World of Harry Potter from 10:00 PM, 13 July to 1:30 AM, 14 July.

From 15 July 2011 at 6:00 AM Eastern through 18 July 2011 at 3:00 AM Eastern, LeakyCon Radio was broadcast by SiriusXM. Several panels were broadcast, as well as information on Pottermore and the Universal Orlando Wizarding World theme park. Anelli was a speaker regarding Pottermore, as she had been working as a consultant on the site since 2009. James Deeley, creative director for Pottermore, headed the presentation.

Among the invited guests were Helena Barlow, Arthur Bowen, Scarlett Byrne, Benedict Clarke, Ellie Darcey-Alden, Rohan Gotobed, Evanna Lynch, Chris Rankin, Ryan Turner, and Will Dunn.

In addition to fan-created and performed musicals The Fountain of Fair Fortune, The Last Battle and The Warlock's Hairy Heart, both StarKid Productions, drawing an audience of 3,000, and Potter Puppet Pals performed live. Keynote speakers included Arthur A. Levine, the U.S. editor for the Harry Potter series, and Electronic Arts, who produced Harry Potter video games. ArtInsights debuted six new prints designed by Stuart Craig and illustrated by Andrew Williamson at the convetion.

Two concerts featuring twelve bands were scheduled. LeakyCon 2011: Live at the Leaky Cauldron II, a collection of 33 tracks from performances at the convention, was released on 17 August 2016 and featured Draco and the Malfoys, Lauren Fairweather, Gred and Forge, Hank Green, Harry and the Potters, The House of Black, Justin Finch-Fletchley and the Sugar Quills, MC Kreacher, The Parselmouths, Tonks and the Aurors, and The Whomping Willows. Evanna Lynch was featured on the final track, with Harry and the Potters.

A literary track was introduced to LeakyCon in 2011, which was organised by Maureen Johnson.