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In September 2019, BCS granted Humphries' request to be released from their program, and she began to compete for the United States.

In September 2019, she married American former bobsledder Travis Armbruster in California.

In 2018, Humphries filed harassment complaints against Bobsleigh Canada Skeleton head coach Todd Hays, high performance director Chris Le Bihan and president Sarah Storey. Humphries petitioned to be freed as it was a requirement from the IBSF, though she had no contractual obligations to BCS, in order to compete with the United States' bobsleigh team. BCS refused to release her for competitive reasons, which lead to a law suit and a filing with the SDRCC. An independent investigation by Hill Advisory Inc. which was hired and paid for by BCS, concluded in September 2019 that there was not enough evidence to convict M.Hays , Mr.Lebihan or Ms.Storey. During the investigation Humphries submitted a list of conditions, after Bobsleigh Canada requested the list as a return to sport plan under which she would be willing to compete for BCS. The list consisted of five pages citing requests that would have cost tens of thousands of dollars to BCS' budget, including retroactive carding money that was pulled 2 months after she filed her initial harassment claim, an additional full time pilot coach, a part time push coach (to become full time in an Olympic year), additional therapist, and a replacement high performance director through the Canadian Sport Institute Calgary to prevent further contact with Hays, Le Bihan and Storey. BCS refused the conditions, after months of deliberation, although they were items that had previously been supported years before.

On January 9, 2016, Humphries became the first woman to drive an all-female team against men in a four-person World Cup bobsled race; her teammates were Cynthia Appiah, Genevieve Thibault and Melissa Lotholz.

On January 9, 2016, Humphries became the first woman to drive an all-female team against men in a four-person World Cup bobsled race; her teammates were Cynthia Appiah, Genevieve Thibault and Melissa Lotholz. Although they finished last Humphries said the purpose was to help get a four-woman bobsleigh division added to the Olympics. Humphries knew their entry would not be a contender due to the 300-pound weight difference between her team and the all-men teams.

In 2014, Humphries and Elana Meyers became the first women to pilot a mixed-gender team in the first international four-man bobsleigh competition to allow women to compete with/against men. As of the end of the 2013–14 World Cup season, Humphries has won 28 Fédération Internationale de Bobsleigh et de Tobogganing (FIBT) World Cup medals, 7 FIBT World Championships medals, and 3 Olympic Games medals. Humphries received the 2014 Lou Marsh Award, given annually to Canada's top athlete.

In September 2014, the Fédération Internationale de Bobsleigh et de Tobogganing announced that they would allow mixed-gender crews to compete in four-man bobsleigh. On November 1, 2014, Humphries piloted a mixed-gender team to the bronze medal in the Canadian four-man bobsleigh championships, allowing her team to join crews led by Justin Kripps and Chris Spring as official Canadian entries on the international circuit.

On November 15, 2014, Humphries and Elana Meyers of the United States became the first women to compete with/against men in an international four-man bobsleigh competition, in the season-opening North American Cup race in Park City, Utah. Humphries piloted her mixed-gender sled to a sixth-place finish, Meyers piloted hers to seventh. Later the same month Humphries and Meyers became the first women to win medals in international four-man bobsleigh competition when they finished second and third in the first of two North American Cup races at the Calgary track.

Humphries won the 2014 Lou Marsh Award in December 2014 as Canada's top athlete for the year.

She was married to Dan Humphries, a former bobsledder who competed for Great Britain and Canada. However the pair divorced before the 2014 Olympics and Kaillie may or may not return to her maiden name of Simundson.

The 2013–14 World Cup season saw Humphries reunited with her Vancouver 2010 teammate, Heather Moyse. Humphries would extend her podium streak to 15 consecutive, with a win in the first race of the 2013–14 season and a silver in the second race – an unbroken medal-winning streak of 11 gold medals, 2 silver medals and 2 bronze medals from the end of 2011–12 to the start of 2013–14. Humphries ran well through the entire 2013–14 World Cup series, trading podium positions with the American team of pilot Elana Meyers and brakeman Lauryn Williams throughout the season, with Humphries winning her second consecutive World Cup season title.

This close 2013–14 contest between the Canadians and Americans carried into the 2014 Sochi Olympics competition. Meyers and Williams led after Day 1 of competition having produced two runs built on track record push starts that uncharacteristically beat out the Canadian team at what was their strong suit. Despite being beaten on the start times, Humphries made fewer driving errors and produced cleaner runs but was still just over two-tenths of a second back from the lead time. On the second day of competition, the Americans again won out on quick starting pushes but made several driving errors on the technical course. Humphries' clean piloting propelled the Canadians from second place into the gold medal position, allowing them to become the first female bobsleigh team to repeat as Olympic champions, the first female Canadian Olympians to repeat as champions since Catriona Le May Doan, and etching their names into Olympic history. Humphries said of the record setting achievement: "How do you describe achieving a dream? This is a four-year goal of ours. This has been something that we've done together. Winning gold is amazing, but walking away satisfied is better. After the third run I knew that if we did the business we could be on top."

Humphries, with new brakeman Chelsea Valois, was the dominant pilot during the 2012–13 Bobsleigh World Cup season. The pair finished on the podium at all nine races that season, including a historic five straight wins from the start of the season. They won the overall season championship with a record 1,960 points on a season of six gold, a silver and two bronze medal finishes.

Humphries' success in the winter of 2012–13 included a repeat as World Champion, placing first while setting a track record at the 2013 FIBT World Championship race in St. Moritz. This win meant that Humphries finished on the podium in all 10 FIBT races during 2012–13, while extending her consecutive FIBT podium finishes to 13 when counting the last two races of the 2011–12 World Cup season plus the 2012 FIBT World Championship race. This streak of 13 consecutive podiums over two seasons included a run of eight consecutive wins from the end of 2011–12 through the start of 2012–13, while teamed with three different brakemen (Baadsvik for one win, Ciochetti for two wins and Valois for six wins/ten podiums).

Humphries teamed up with brakeman Emily Baadsvik, then brakeman Jennifer Ciochetti, for the consecutive wins in the last two races of the 2011–12 World Cup season. Humphries and Ciochetti also won the 2012 World Championship race in Lake Placid, adding a World Championship to Humphries' Olympic Championship. This was also the first gold for any Canadian woman's sled team at the World Championships. When asked about what her result means on top of her Olympic gold she said that "It feels amazing. It is another goal accomplished. This means a lot to me. I feel like I'm still growing as a pilot and I try to learn from every experience. I have been working on my consistency and I'm glad it showed here." In the team event, Humphries went on to help guide the Canadians to a bronze medal as well, adding to her medal tally that year.

Humphries' three gold medals to finish the winter of 2011–12 was the start of a winning streak that would eventually break records for woman's bobsleigh competition.

The "I've Been Bullied" campaign warns people of the long-term effects of bullying. She speaks about her personal experience as a victim of bullying, and she discusses the importance of avoiding bullying in any sports. "Right to Play" is an organization that uses sport and play as a way to "educate and empower" children facing difficulties such as disease and conflict. She is in this organization with the other Canadian Olympic gold medallist, gymnast Kyle Shewfelt. Humphries and Shewfelt brought equipment for sports and set up some sports programs for the underprivileged children and youth when Humphries and Shewfelt traveled to Liberia in April 2011. They want to give some of the children a chance to change their lives. In the Special Olympics, Humphries speaks regularly at a few elementary schools at Calgary about the importance of physical activity, setting goals, and saying "no" to drugs.

After the 2010 Olympic win, Humphries met with less success on the World Cup tour and in World Championship competition for nearly two seasons. She only finished on the podium once during the 2010–11 World Cup season, though her consistent top-10 finishes allowed her to finish in third place for the overall season. Humphries slid to fifth place for the overall 2011–12 World Cup season, though she did have four podium finishes, including three gold medals, by the end of the season.

Following a seventh-place finish in 2009-10 Bobsleigh World Cup season series, Humphries ran well throughout the 2009-10 Bobsleigh World Cup season, finishing second overall with one win, two other podium finishes, and never less than a top-six finish (in a field of 20) over the eight-race season.

Humphries 2009–10 World Cup season prepared her for the first prominent achievement of her career—winning the gold medal in the Two-woman competition at the 2010 Winter Olympics, with her 2009–10 brakeman Heather Moyse. The silver medal was won by fellow Canadians Shelley-Ann Brown and Helen Upperton. It marked the first time of the 2010 Olympics that Canadians had won two medals in one event. The win completed a childhood dream for Humphries. After the final run she said that "I don't think I can put it into words yet, we did our job, you know. The goal I set as a little kid, to have done it, is amazing."

In 2007, Humphries was placed low on the Canadian depth chart and did not feature at the 2006 Winter Olympics. In an effort to compete she considered representing the United Kingdom, the country of her then-fiancé, Dan Humphries. Opting to remain with the Canadian team, she gained a spot on the roster after signing up for a bobsleigh driving school. She won the silver medal in the mixed bobsleigh-skeleton team event at the 2008 FIBT World Championships in Altenberg, Germany.

Humphries did not start as a bobsledder but competed in alpine ski racing before the age of 16. After breaking both legs in separate crashes, she retired from the sport. In 2002 Humphries began her bobsleigh career as a brakeman, and was an alternate to the Canadian team at the 2006 Olympic Winter Games in Torino.

Kaillie Humphries (born Kaillie Simundson September 4, 1985) is a Canadian-born bobsledder who currently represents the United States. Representing Canada, Humphries is a two-time Olympic champion in the two-woman (2010, 2014), and is the 2018 Olympic bronze medalist with brakeman Phylicia George. With her victory in 2014, she became the first female bobsledder to defend her Olympic title. Due to her repeat championship, she was named flagbearer for the closing ceremonies at the 2014 Olympic Games together with brakewoman Heather Moyse. Humphries is also the two-time defending overall World Cup champion. To date, she is the most successful Canadian bobsledder in history. In 2019, she switched to representing the United States because of abuse and harassment that she claims she faced from the Canadian bobsled federation.