Here are some theories I have towards how Lion Guard could fit into The Lion King 2 Simba's Pride and the Lion King series as a whole

1) Quite simply they were off on another mission, which is not far fetch'd if you think about it. I mean, its like the Avengers, of which this show is partly inspired by: If the Avengers were responsible for helping out EVERY "big problem", then what would be the point of every other superhero existing in Marvel like the X-men, Spider-Man, SHIELD itself etc.? They specifically can't always help out EVERY problem of course. Besides, the Pride Lands and Africa itself is a HUGE place so they could have just been busy with something else.
2) Possibly, because of Kion's friendship with hyena Jasiri, of which Simba does not currently know about. Maybe its a scenario where when Kion got older there was a misunderstanding with that Jasiri could have done something and Kion had an argument with Simba over it, and Kion just ran away with her because "we are the same", which would further motivate Kiara to prove Kovu's innocence and her independence when she got older
3) Very possibly, like with Simba and Nala's original son Kopa in the Lion King books, Kion went off to form his own Pride, or even Lion Guard somewhere else outside the Pride Lands. Like I said, Africa is a huge continent after all, and the series is said to be set in Kenya, so Kion and the Lion Guard could have moved to another part of Africa. There is also a chance that Bunga could have persuaded them all to "Hakuna Matata" it all when they got older, like his uncles
As you can see, its pretty much common sense as to how it can still tie into the series. They were able to make Megara appear on an episode of Hercules: The Animated Series, which is a midquel series like this and they were still able to make it work without ruining the continuity, so they could find a way to make it work here. As Kovu and the Outsiders are going to appear on the show, it is likely that they will find a way to tie it all in together, perhaps by the series finale if nothing else.

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While all your theories are interesting Pixarer, both The Lion King II: Simba's Pride and the new TV show The Lion Guard are non-canon, meaning both of them never really never happened. The studio that makes the canon keeps the canon, for example Walt Disney Animation Studios made The Lion King, but then DisneyToon, a different studio made The Lion King II: Simba's Pride, which means it is non-canon since WDAS didn't make it, the same applies for The Lion Guard it wasn't made by WDAS. WDAS made the canon, which means they keep it, so I don't think it will even matter if they all tie together, especially since the end result isn't even canon. As for those Lion King books you mentioned those two are non-canon and I did some research and found they weren't even published by Disney, or even approved by them, and are completly non-canon.

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Overall to Disney they are still canon even if they are not made by WDFA as Disney acknowledges the content in their merchandising and in official products such as story books and continuing spin offs/sequels like this even if it may appear to create continuity problems like this. Unless it is officially retconned or meant to obviously be non-canocial like house of mouse then everything Disney does with their characters in a visual media sequel (TV, movies, sometimes video games), then they are still considered canon to the overall story of the original movie.
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Actually Pixarer, they are not. While Disney continues to provide merchandise for the film. Disney employees have openly stated that Disneytoon films are not canon, including one Disney employee, Keith Lapinig. I myself have done some extensive research, and have found many articles and a video by Keith Lapinig who explains it in the best way possible- 

-The Rescuers (WDAS) to The Rescuers Down Under (WDAS)=both are canon 
-The Little Mermaid (WDAS) to The Little Mermaid II (DTS)=The Little Mermaid is canon, but not it's sequel
-Frozen (WDAS) to Frozen Fever (WDAS)=both are canon

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Another explanation could be that Kion and the Lion Guard could have been out looking for other lions to help Simba & co against Zira, and that these lions would produce the next generation of Lion Guard.
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I know I'm usually here for the Finding Dory stuff, but I couldn't resist checking out this thread, seeing as how I, too, have a theory as to how the Lion King universe all fits together, which I'll get to in a second.

@Arlo, there's no need to be a buzzkill, Pixarer was just having a little fun with some world-building. Just because something isn't considered to be "officially canon" doesn't mean we still can't have fun with it. Franchises have alternate canons and universes all the time, and part of the fun of being a fan is seeing how these storylines may (or may not) coincide, no matter how crazy the theory may be. If you don't think the sequel films are canon, that's fine, but it's good to let those who do think they are canon have their fun.

On that note, I'll get into my personal TLK theory, and what a better day to post it, seeing as how Disney just announced their live-action Lion King today! 

My theory needs quite a bit of explanation, but what it boils down to is this: The cub at the end of the first movie is actually Kion.

At the beginning of Scar's reign, an outsider pride of lions, led by Zira, offer to move into Pride Rock. Although Scar's Pridelands are bad enough, Zira's family was living in conditions much worse. Also, Zira is pregnant with Kovu and is in need of a stepfather to take care of young Nuka and baby Vitani after her mate had recently passed away. Gracious to have lions that respect him, Scar agrees to help these new followers. Once Kovu is born, Scar chooses him as his new heir and takes him under his wing. 

As the condition of the land gets worse and worse, Scar forces both the hyenas and Mufasa's pride to stay within the boundaries of the Pridelands, but secretly gives permission to Zira's family to leave and find more food. Zira's pride is gone for a very long time, so long in fact that when they return, Scar has been defeated and Simba and Nala have had their firstborn son, Kion.

Simba is furious towards these followers of Scar and commands them to be banished the Outlands. Zira agrees, but not before secretly kidnapping baby Kion and taking him with her. Once Simba realizes that his son is missing, he journeys to the Outlands and, through a series of misunderstandings, is convinced that Kion was killed by Zira. 

The royal family is heartbroken until Nala reveals that she's pregnant with another child. Since Simba and Nala's first cub was killed so early in its life, this new cub (Kiara) would be next in line for the throne. Kiara's birth and presentation go off without a hitch, and Simba decides, for the good of his daughter, to never, ever mention Kion. Later in her childhood, Kiara encounters a young Kovu in the Outlands.

As it turns out, Kion wasn't killed by Zira after all. Despite still being a baby cub, he managed to escape Zira's pride but soon got lost far beyond the Pridelands. Luckily, he managed to survive on his own, and after a year or two, grew into a young cub and made it back to Pride Rock to an overjoyed Simba and Nala.

Kiara has also grown into a young cub (about six months younger than Kion), and while she is at first excited over that fact that she now has a brother, she soon becomes upset, as this means she's no longer a princess. A ceremony is planned for Kion to reclaim his title as prince, but Kiara is still heartbroken over the loss of her own title. Out of the goodness of his heart, Kion decides to let Kiara keep her role as princess, making her the new future queen. This leaves Kion out of a job, until he eventually forms the new Lion Guard.

[The bulk of The Lion Guard picks up from here. This last paragraph takes place after Lion Guard's timeline, during the later events of Lion King 2]

Everyone, including Kiara, Kion, and the Lion Guard, eventually grow older. A couple weeks before Kiara's first hunt, word comes to Pride Rock that the hyenas have relocated from the Outlands to the faraway jungle where Simba grew up. Dissatisfied with their failures in the Pridelands, the hyenas decided to go to a place where there is no Lion Guard, so they can feast on the animals there instead. Upset that they have to leave the Pridelands behind but determined to protect the jungle paradise, Kion and the Guard depart their home to defend the faraway land from the invaders.

While the guard is away "at war," the bulk of the events of TLK2 take place. This also explains why there are no hyenas in the sequel. Kion and the Guard don't return to the Pridelands until after the events of TLK2.

So, that's my explanation. It's pretty lengthy and requires some disbelief suspension, but it fills in all the plot holes it needs to. If anyone else has any other ideas, feel free to post them!
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(Disney i love you, but one Ressiance remake is just enough, please)

I really got into The Lion Guard too late in it's run, i have the pilot movie on DVD, and im looking forward to buying the episodes on DVD, i sadly don't have the channel the shows airs (I have Disney Channel, which airs the show on mornings) and yet i dont understand, how can it does well

I think some Disney stories are canon and some are not, the DTV movies are in the sets of midquel (Lilo and Stitch 2, Bambi 2), prequels (Tarzan 2, The Little Mermaid: Ariel's Beginning), and sequels (many of them)

I dont hate The Lion Guard nor the DTV movies, this is just my opinion
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