[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/pga_heartwarming.jpg]]
[[caption-width-right:350:''"I'll always be with you."'']]

''Pooh's Grand Adventure'' has plenty of moments that reduce your heart to mush.

'''As a Moments subpage, all spoilers are unmarked [[Administrivia/SpoilersOff as per policy.]] Administrivia/YouHaveBeenWarned.'''
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* The Gorge scene is a series of these in spite of the danger. First, when Tigger is trapped and can't muster the confidence to even try to bounce, Pooh is constantly trying to encourage him. When Pooh falls in, Piglet (who earlier bemoaned his complete lack of courage) leaps after him without any hesitation. When the small root that Piglet is holding onto breaks, Rabbit then leaps in also without any hesitation, completely abandoning the map in the process. It's especially poignant with Rabbit when you think about the fact that he'd just sung a song that was all about praising the map and highlighting its importance. But when his friends are in trouble, all thought about that small piece of paper leaves Rabbit and he doesn't even think for one second about trying to hold onto it if it'll impede his attempt to save his friends.
** Tigger taking Pooh's hand and his grip tightening as he holds on for dear life when the log falls.
* Even though Rabbit’s adherence to the map is clearly not helping them in this situation since he’s flagrantly ignoring the Forbidden Mountains, the group recognizes how important the map is to him and tries to save it, if not just for the group’s sake. Tigger immediately takes point chasing after the map, and before he’s dragged into the chain of friends, Eeyore tries to grab it even when Rabbit has abandoned it to go after the others.
* "Wherever You Are" has the tendency of bringing tears to your eyes. The relationship between Pooh and Christopher Robin is so undeniably ''[[IncorruptiblePurePureness pure]]'' that you can't help but admire it.
** Also, at the end of the song, when Rabbit gives a sleeping Pooh the map as a blanket. [[JerkWithAHeartOfGold From him]], it is moving to tears.
** The end credit version of the song performed by Vonda Shepard & Barry Coffing is also heartwarming & tearjerking; it gives you tears of happiness ''and'' sorrow.
* It's extremely subtle, but the small friendship between Eeyore and Piglet. It's quite heartwarming to see Piglet walking and holding onto Eeyore's tail, and then the two huddled together while they sleep.
* The gang overcoming their various flaws in order to get to Christopher Robin, all in the name of Pooh, who at this point they think is dead.
** [[TrueCompanions The utter dedication they all have to each other]] in their DarkestHour, whether they were VitriolicBestBuds like Tigger and Rabbit or somewhat distant friends like Eeyore and Rabbit, is heartwarming. Especially when the gang helps Rabbit up after he nearly falls into an abyss in Skull or when the others pull Eeyore up to the Eye of Skull.
** When the group succeeds in getting a way to the Eye, Piglet hears Pooh’s cries as he falls further into the cave and mistakes them for his imagination. He tells Rabbit and Eeyore that he could’ve sworn he heard Pooh cheering them on even though he’s seemingly dead. And Rabbit looks surprised, but gently nods in a parental way.
* When Pooh gets trapped all alone in the cave, simply remembering Christopher Robin's voice is enough to cheer him up.
** Once he'd been trapped, he immediately tries to escape so he can try to help his friends.
* We find out in the end that the sounds of the "Skullasaurus" were actually Pooh's stomach rumbling due to having not eaten any honey since he had last seen Christopher Robin. Throughout the entire adventure Pooh had the pot Christopher Robin had left him but he refused to eat it because all Pooh could think about was finding him and the honey pot was the only thing he had to remember him. The fact that Winnie the Pooh who normally only thinks about satisfying his bottomless appetite for Honey was able to completely, if subconsciously, ignore his hunger for nearly two days straight speaks volume as to how heart-set he was in finding his best friend.
* Once the other four are reunited in the crystal caverns of Skull, Piglet happily exclaims his friends' names, delighted to be reunited with them.
* The group reuniting with Christopher Robin, believing they've succeeding in finding and saving their friend after overcoming their vices. They also give Christopher Robin some credit believing he was able to escape the Skullasaurus on his own somehow, with Rabbit praising him for his cleverness, Tigger for his strength, and Piglet for his bravery. Christopher Robin also pets Eeyore's head.
** Given how Christopher later says he thought of the first three when he was trying to find the strength, bravery, and smarts to go on, the approval and praise from his childhood friends surely meant a lot even if he was never in the danger they thought he was.
* Pooh finally reuniting with Christopher Robin. For a few precious moments, [[SilenceIsGolden neither of them say a word]], but Christopher just smiles at his bear to comfort him now knowing the traumatic adventure he's endured. And Pooh looks in shock at Christopher, clearly having not expected to see him again in person... and gasps as he embraces him, relieved to finally have him back all the same. Christopher tops off their reunion with a "silly old bear".
* "Everything Is Right", showing the gang's happy, safe return home and bidding farewell to each other.
** Everyone confidently marches home, the scary locations turning out to have been exaggerated by their own fears and imaginations. The group even helps Pooh get some honey on the way home and carry him and Christopher out of a stream.
** The last we see of Piglet is him atop the tree at his house with no issues, the last we see of Rabbit is him with his harvest underway, and the last we see of Tiger is him bouncing over his house and waving goodbye. All three have overcome their vices and can now live happy, content lives having done so now that their friend is safe and sound.
** Eeyore also retires back to his home he repairs, and even Owl swoops in for one last cameo praising everyone for saving Christopher Robin. Owl evidently is not nearly as attached or dependent on Christopher as the others, but he still is happy that the boy has been rescued from, as far as he knew, mortal peril and that the others have him back.
** The very last we see of Piglet, Tigger, and Rabbit is of them waving goodbye to Pooh and Christopher Robin, which almost feels like they're waving goodbye to the audience after taking such a harrowing, epic journey with them. The song ends with Christopher walking to Pooh’s house to take him home at last.
* When Christopher Robin notes he'll be leaving for School again the next day, Pooh succinctly asks "Shall I look for you ''again''?". He already went through hell to find Christopher Robin once, but will gladly do it as many times as he has to so they may stay together.
* When Pooh and Piglet are being carried away by the butterflies, Pooh drops the honey pot, and Tigger immediately bounces to catch it before it hits the ground despite hating honey himself. Tigger knows just how important it is to Pooh.
* When Rabbit breaks down and admits he has gotten them lost, the others just look on with empathetic sadness and tell Rabbit they have all done no better. Tigger's expression is especially sweet, as he looks so understanding and sympathetic.
-->'''Rabbit:''' I don't know where we are, and where we aren't. And I haven't known for hours. ''*sighs*'' I've failed us all.
-->'''Pooh:''' ''*pats Rabbit's shoulder*'' I believe I have as well.
* The film isn't that known in the mainstream media, but the ArcWords from Christopher Robin are among the most well-known and beloved ''Winnie the Pooh'' quotes out there, even if they are mistakenly attributed to A.A. Milne.
* The ending of the film, in which Pooh and Christopher Robin reflect on their adventures apart from each other. Christopher Robin says that when he didn't feel smart, brave, or strong enough, he'd think of Rabbit, Piglet, and Tigger respectively. But when he felt alone, he thought of Pooh. The scene then transitions into perhaps the best adaptation of the ending of the original Milne stories, in which Pooh promises that he will always be with Christopher Robin, forever and ever. The film then zooms out as the narrator explains that we will always find them in the Hundred Acre Wood, dusk having fallen, and Pooh and Christopher Robin remain on the hill embracing as the film ends.
-->'''Christopher Robin:''' Promise me you'll be here, always? Even when I'm a hundred?
-->'''Pooh:''' ''*ponders for a moment*'' How old shall I be then?
-->'''Christopher Robin:''' Ninety-nine.
-->'''Pooh:''' I promise.
-->'''Christopher Robin:''' Forever and ever?
-->'''Pooh:''' Yes, Christopher Robin. Forever and ever.
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