* AntiClimaxBoss: Multiple examples, almost all of whom fight alone in a game where 3 on 3 battles are standard.
** The Chaos Lord is built up to be the evil prince of Digimon that the humans were forced to flee to another continent from. Turns out he's just a Machinedramon PaletteSwap that fights alone. Even though he has a nasty main attack that allows him to attack multiple times in one turn, most of the battle consists of him either guarding or using weak secondary attacks which also lower your attack, creating a side effect of needlessly prolonging an otherwise pathetic battle.
** Much like the above example, [[spoiler:Neo-Crimson]] is a pushover despite having the combined power of the three Chaos Generals. Like the Chaos Lord, he fights alone, plus his secondary attacks are pretty weak, and his main attack has a chance of hitting ''himself''. The previous two battles against him were much more challenging.
* ContestedSequel: While the game does have its fans, not everyone was happy with the switch from the first game's open world exploration and monster raising elements to a dungeon crawler roguelike. It tends to get a lot of criticism for its mechanics (which result in a lot of mandatory grinding) and generally slow pace.
* DemonicSpiders:
** All Digimon capable of causing confusion fall under this trope due to effectively rendering your team unable to do anything but beat themselves to death, but three in particular stand out.
*** First is Raremon, thanks to his main Counter skill, Buffalo Breath. If you attack him and trigger his counter, it will ''always'' confuse you, unlike other attacks that only have a chance to do so. Worst of all, there are no less than ''three'' mandatory fights featuring a Raremon, including one in the Coliseum where you cannot even use items to remove confusion. Better hope you have at least one party member with an Interrupt skill.
*** Then you have Bakemon. If you get into a fight with him in the wild, you will not be able to run away, no matter how much your Digimon outlevel him, as he is specifically programmed to prevent you from doing so. Oh, and he moves two spaces for every one you move, making it that much harder to avoid him and his confusion-causing Evil Charm. The only saving grace is that he travels alone, making it easy to take him out... if he doesn't confuse you first.
*** Finally, there's [=PlatinumSukamon=]. While his attacks don't directly cause confusion, he has a nasty Assist skill, Panic Wave, that causes himself or one of his allies to gain confusion power — that is, ''guaranteed confusion with every single attack''. Not helped by the fact that he usually travels with Kuwagamon and his dreaded Scissor Claw. Speaking of...
** Kuwagamon and Okuwamon also fit this trope, thanks to their respective Scissor Claw and Duo Scissor Claw techniques, both of which lower your Digimon's defense, while the latter does it to ''all'' of your Digimon. It doesn't help that they also frequently travel with other dangerous Digimon — Kuwagamon can often be found with [=PlatinumSukamon=] as mentioned above, while Okuwamon tends to hang out with heavy-hitting Digimon such as [=MetalTyrannomon=], or those with annoying attacks such as Etemon.
** Kabuterimon and his subsequent Digivolutions also count, mainly due to their primary techniques being Interrupts that affect your own techniques by either dramatically reducing their damage or even ''making them miss altogether''.
** Soft Domain marks the first appearance of wild Mega Digimon, but the most notable of them is [=MetalSeadramon=]. Apart from being able to move two squares for every one you move, he can also be difficult to run away from if he does manage to catch up to you. And if the fight against his Chaos General counterpart in Mega Domain was anything to go by, he's also a tough customer in battle, with decent defense and speed ratings, and a fairly damaging AreaOfEffect attack. And if you thought that was bad, near the end of the game he may sometimes travel with Preciomon, a fast and dangerous Digimon with an even ''more'' painful [=AoE=] attack that usually hits in the 70s-80s.
** Machinedramon, the former FinalBoss of [[VideoGame/DigimonWorld the first game]], appears in this game as a normal enemy. While you won't see him until near the endgame, woe betide you when you do. In addition to high HP and defense, his primary attack, Giga Cannon, allows him to attack you repeatedly, ''multiple times in one turn''. And [[TheComputerIsACheatingBastard unlike you]], he can just use it again the next turn without having to guard or regain his MP. If you're really unlucky, you might end up having to fight ''two'' Machinedramon at once in [[spoiler:the Chaos Tower or Tera Domain]] – an almost guaranteed GameOver if you don't have any HP Drivers or high-level healing skills at hand to outpace their sheer damage. Luckily, that particular encounter is fairly rare, and the Puppetmon they travel with [[CowardlyMooks tends to run away from you rather than confront you]].
* GameBreaker:
** Okuwamon's aforementioned Duo Scissor Claw technique. It damages an entire enemy team and lowers their defense at the same time, and the defense-lowering effect ''stacks'' up to two times. You could potentially have an entire party with the attack (easily done with DNA Digivolution) and shred every boss by using it twice at the start of a fight, and then switching to stronger attacks afterwards. Techniques that apply debuffs in general are rather strong in this game. Even the single-target counterpart, Scissor Claw, learned by his predecessor, Kuwagamon, is highly useful in the earlier stages of the game, and can even be acquired as early as Disk Domain, where you can befriend and digivolve a Kunemon.
** Interrupt techniques have a distinct advantage in that they don't trigger Counter Attacks. This includes particularly annoying ones such as Raremon's Buffalo Breath, which won't confuse you if the counter isn't activated. This means you can save him for last when he appears, and then use your interrupt on him and guard with your other Digimon, bypassing the confusion problem altogether. Of particular note is the aforementioned Kabuterimon line's Interrupts, which lower the technique's attack power significantly or even force it to miss completely, meaning you barely take any damage. The only drawbacks are that you can only use one Interrupt per turn, and you can't interrupt an activated Counter Attack.
* GoddamnedBats: Digimon that move two spaces in Domains for every one space you move, such as Birdramon and Bakemon (the latter of which is specifically programmed to be impossible to run from when in battle), tend to fall into this category if you're trying to avoid battles. Most of the time, the rooms you encounter them in aren't big enough for you to escape them, and in many cases, you'll enter a room and immediately find yourself cornered by them. Some of the later ones, such as [=MetalSeadramon=] and Piedmon, even tread DemonicSpiders territory. Getting them to join you is an even ''harder'' task, and one that you're in fact required to do when Professor Piyotte asks you to recruit an Ikakkumon, who only hangs out with Birdramon.
* HilariousInHindsight: A lot of things this game was mocked for at the time later became canon in the anime.
* ScrappyMechanic:
** The need to constantly DNA digivolve and grind your lower level mons back up to a usable level to progress is one of the more criticized aspects of the game due to it introducing a large amount of ForcedLevelGrinding, not helped by the game's generally slow pace in its load times and walking/battle animations making it take even longer.
** Recruiting certain Digimon can be a very annoying process. It requires you to fire gifts at them in the field, then battle and defeat them (in a team with multiple Digimon, the one which is KO'd last is the one who joins), but the gifts are separated by the three types. Initially, only the team the player chose will have gifts available for that type. It isn't until the Device Dome that the player can reliably get Digimon of the other two types and even then they're restricted to low-level gifts for a large part of the game.
*** Also, due to the aforementioned variation in enemy Digimon movement, depending on the kind of Digimon you want, it can be really hard to be able to fire enough gifts to get them to join you, as they simply don't give you enough opportunities to fire enough gifts. It is possible to get lucky sometimes and get them caught behind a trap that they can't move past, but even outside of needing luck not every Digimon group spawns in a floor configuration that allows this to happen in the first place. Further compounding this is the fact that Digimon can randomly "ignore" gifts, wasting them and possibly screwing you over. This becomes especially annoying in the Piyotte requests, which are mandatory to complete the game, with Ikkakumon being in a group with Birdramon who moves two squares per action, all but mandating a rare high-level "Toy" gift or trapping them behind a rock.
** The various traps that generate in dungeons, especially earlier in the game when your means of dealing with them are extremely limited if not outright unavailable. Sure, you can upgrade your systems to detect and remove them as the game progresses, but many of those upgrades are not available until much later in the game, and you'll often encounter traps that you cannot even destroy with your current systems/upgrades. Worse yet, sometimes the dungeon may generate an ''unavoidable'' trap that you can't get rid of. Should that happen, you're forced to either run into it and tank its effects or abandon the dungeon and start all over. Not to mention that sometimes traps may sometimes slip past your detection systems if it's an equivalent or higher level, and you won't know it's there until you step on it.
*** Special note goes to Bug Nests, and in particular, Return Bugs. If you step on one by accident, it will begin randomly kicking your Digimon out of your Digi-Beetle and returning them to the Server. Thankfully, they stay in your Digi-Beetle much shorter than the other three Bugs - if you're lucky, they might even leave after returning only one Digimon, but many times it will be one of your main Digimon, all but ruining your run. In worst case scenarios, you end up having ''all but one'' of your Digimon sent back. At least you can kick them out immediately by using an appropriately levelled Return Bug Zap item, but in most cases the damage will have been done and you'll be forced to abandon the Domain to retrieve your Digimon, then dive back in... only to have the same thing happen again. [[note]]Surprisingly, you ''can'' actually prevent Return Bugs from invading your Digi-Beetle by filling the Server to capacity with junk Digimon (such as low level Rookies), as they cannot return your Digimon if the Server is full, but it would take [[AwesomeButImpractical far more time and gifts]] than the [[IncrediblyLamePun return]] would be worth.[[/note]]
*** Bit Bugs can be pretty devastating too if you don't have a lot of money, as they gradually eat your money as you move, and then proceed to sabotage your Digi-Beetle's parts when they run you dry. This isn't as much of a problem in the later game when you're more likely to have a beefier wallet (unless you've been spending most of it upgrading your Digi-Beetle or trying to befriend a specific Digimon), but in the early game, especially after you start encountering level 2 Bit Bugs, you could see this happen more often than you think.
* ThatOneAttack:
** ANY attack that causes confusion is one of these, especially Raremon's Buffalo Breath, a counter technique that always causes it. It almost always affects the player's Digimon, causes said Digimon to randomly attack the rest of the party and themselves for much more damage than the enemy is capable of causing, and can potentially last the entire fight, turning what would otherwise be a ForegoneVictory into a long drawn out slugfest as you try to defeat the enemy before your own confused Digimon [[HoistByHisOwnPetard knock themselves out]]. Even using items or status recovery techniques (such as Tinmon's Recovery Power) to cure it won't help much, because you can just get confused all over again. Fortunately, you can bypass it somewhat by using Interrupt techniques such as Garudamon's Wing Blade.
** AreaOfEffect attacks in general follow this rule as well if you're on the receiving end. Okuwamon's Duo Scissor Claw, Whamon's Tidal Wave, and pretty much any Mega-level [=AoE=] attack come to mind very quickly. On the flip side, however, getting hit by an [=AoE=] allows you to get guaranteed Counter Attacks off.
** [=ExTyrannomon=]'s Pretty Attack, Etemon's Concert Crush, and [=MarineAngemon=]'s Ocean Love. These techniques lower your Digimon's "motivation", stopping them from using their two most powerful techs. If you haven't DNA Digivolved your Digimon enough, it can be very debilitating in boss battles where you need to maintain constant damage output. It is most noticeable in the first fight against [[ThatOneBoss Crimson]], who uses an [=ExTyrannomon=].
** Machinedramon's Giga Cannon, when used by the AI. When the AI uses it, they attack a random number of times in a row, dealing quite a bit of damage. For comparison, when you use it, you attack repeatedly until you run out of MP, at which point you're forced to either Guard or use MP-restoring items. The AI can just immediately use it again the next turn [[TheComputerIsACheatingBastard due to having unlimited MP]]. The Machinedramon-like [[spoiler:Chaos Lord]] uses a similar attack during his boss fight.
* ThatOneBoss:
** Crimson. When you fight him as the DiscOneFinalBoss, he is by far the most powerful fight in the game. Unlike Damien who (being the first person to use a Mega against you) brought a rather pathetic Puppetmon, Crimson brings a mighty [=SkullMammothmon=], one of the tougher Megas in the game. He uses a very powerful AreaOfEffect attack for that point in the game, and his defense and HP more than make up for [[MightyGlacier his slow speed]]. He's especially dangerous if you have a mostly Virus team, since his Vaccine typing gives him the advantage over Virus types. But the problems don't stop there. Crimson also has an [=ExTyrannomon=] in his team, who can prevent your Digimon from using their two most powerful techniques, effectively crippling them and reducing them to dealing ScratchDamage, unless you've done a lot of DNA Digivolving. It's a shame that the next time you fight Crimson, he's actually ''weaker''.
*** But even when you do fight Crimson again [[spoiler:just before the fight against the Chaos Lord]], he's still no letdown. All three of his Digimon in the rematch use [=AoE=] attacks and can deal considerable damage. In addition, his main partner, [=VenomMyotismon=], can also use Venom Infusion, an Interrupt technique that ''completely negates one of your Digimon's attacks''. If this happens as you're trying to use HP Recovery or a similar healing technique when your party is already at critical health, it can easily spell a quick GameOver.
** The sheer amount of minibosses in Data Domain qualify due to all of them featuring confusion attacks, but most notable among them is the fight against the source of all the confusion, [[spoiler: two Gekomon and a [=ShogunGekomon=]]], who will have you almost completely locked in confusion throughout the battle. If your Digimon don't know any Interrupt skills, or if you didn't bring Power Disks or EX Drivers, you're in for a very rough battle.
** The [[InevitableTournament mandatory tournament battles]] can be debilitating at higher ranks, but it gets outright brutal at the Chief Rank, when you face [[spoiler:each of the three Guard Team leaders]] in succession. All three fights feature at least one Mega level Digimon, while the last fight against [[spoiler:Cecilia]] puts you up against ''three'' Megas, one of whom can even ''revive'' one of its teammates. Bear in mind, you have to do this all in a NoDeathRun, plus you can't use any items at all and your Digimon are not healed or revived between fights. Good luck.
* ThatOneLevel:
** Data Domain, for its [[BossRush obscene amount of confusion-based minibosses]]. First, you must face five of your fellow Guard Tamers, who have become mysteriously confused, causing them to attack you with Digimon that know confusion attacks. After returning them to their senses, you must face off against the source of their confusion, [[spoiler:a gang of Gekomon armed to the teeth with even ''more'' confusion attacks]]. It's a shame that the main boss of the domain, [=ChaosPiedmon=], is ''much'' easier than any of these minibosses.
** Soft Domain is filled to the brim with traps and is the first Domain where Mega level Digimon appear (including [=MetalSeadramon=], who moves two squares per action). However, the real kicker is the last part of the very last floor. After the fight with Crimson, in order to get to Chaos Lord, you need to pass through a lengthy corridor of Acid Swamp tiles. If you have not upgraded your Digi-Beetle's tires (or if they are damaged and you didn't bring a Parts Fix), the section is basically impossible to pass through, but even then, there are multiple red acid tiles (the highest and most damaging tier) whose corresponding tires aren't even ''available'' at that point in the game. With each red Acid Swamp dealing 250 damage, this effectively means that you are forced to take considerable damage to reach Chaos Lord, necessitating several Mech Fix EX items to restore your Digi-Beetle's health, or risk having to Auto-Pilot and go through the whole dungeon again. Worse yet, the tiles themselves are randomized — you might be given mostly purple and lower tiles and only a few reds, or you might get 90% red tiles and little to no weaker tiles. To top it all off, up until this point, going through Acid Swamps was generally never ''required'' to clear dungeons, much less going through one that surpasses the tires that are available, so a first-time player is very unlikely to have the necessary items.
** [[spoiler:The [[TheVeryDefinitelyFinalDungeon Chaos Tower]]]]. None of the other Domains are as much a LuckBasedMission as this one, with red-level traps present and in ''much'' higher concentrations than previous Domains - even with a fully-equipped Digi-Beetle, you are extremely likely to hit at least one Land Mine, Electro-Spore, or Bug Nest that your detection systems failed to pick up. Not to mention, it is home to some of the strongest wild Digimon encounters (high level Ultimate and even ''Mega'' Digimon). The creepy, bluish colors of the floors and walls and the [[https://www.youtube.com/watch?v=_23ItCZPJ_0 chaotic, nightmarish music]] certainly don't help matters. And if you somehow manage to make it to the end, [[spoiler:you're greeted by [[FinalBoss Overlord GAIA]], the driving force behind everything, [[ThatOneBoss and he certainly doesn't let down in battle]].]]
* ThatOneSidequest: Any of the trading center quests can be annoying depending on which Guard Team you belong to; as not having access to the highest level gift for a given attribute of Digimon makes capturing them that much harder.
** Trading Garurumon for Magna Angemon requires either using rare (at that point in the game) and expensive gifts in order to recruit a wild one, or being lucky enough to catch it behind an obstacle, which will let you fire as many gifts as you please. Either that, or training your own which is both time consuming and almost guaranteed to be more powerful than the Digimon you get in return. Bonus points if you managed to get Garurumon's {{Palette Swap}}ped cousin G'''u'''rurumon and thought they were the same since it almost impossible to have seen a Garurumon prior to the trade offer.
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