Fans of the Sonic franchise know Miles "Tails" Prower for his intelligence and timid, but caring personality. Back in the 1990s/2000s, Tails played an active role in the games by having his own story (Sonic Adventure) or being playable alongside Sonic and Knuckles (Sonic Adventure 2, Sonic Heroes). Unlike his closest friends, Tails isn't super fast or physically powerful, but that didn't stop him from helping Team Sonic save the day.

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However, as time went on, Tails was slowly pushed out of the spotlight as a playable character in Sonic games to the point where even his personality started to change. His inventions still proved useful, but he's also had a few instances where he wasn't thinking about the bigger picture or was just being difficult for the sake of conflict. Nevertheless, Tails is still an important character regardless of the pen he's being written under.

5 Sonic Lost World: Fixing Cubot

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A running gag since Sonic Colors has involved Eggman's new robot companions: Orbot and Cubot. Specifically, Cubot would have a defunct voicebox that had him speaking in accents until it was fixed...or not. In Sonic Lost World, this happens again when Sonic knocks away the Cacophonic Conch that Eggman was using to control the Zeti. In doing so, the Zeti are able to control Eggman's robots, leading to Cubot losing his body and his voice chip malfunctioning.

There's a scene where Tails fixes Cubot's voice chip and another where he tries putting Cubot on a fallen battle bot just so Cubot can have a body. This ends up being a foolish idea because Cubot's new body responds on its own and tries to attack Tails while he's distracted. Luckily, Eggman saves him from Cubot, and Sonic destroys the battle bot's body, freeing Cubot of his "brainwashing."

While Tails' heart was in the right place, it was rash thinking that could have gotten him and the others hurt. Tails has fought against Eggman countless times, so it's questionable why he thought it would be safe to install Cubot's head onto a robot that's programmed to attack him and Sonic.

4 Sonic Forces: Watching Instead Of Fighting

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At the beginning of Sonic Forces, Sonic saves Tails and a group of citizens from Eggman. A new enemy named Infinite arrives to assist Eggman, along with Shadow, Zavok, Chaos, and Metal Sonic. True identities aside, they all partake in attacking Sonic and end up knocking him out, giving Eggman the chance to take him prisoner.

Meanwhile, as Sonic's fighting, Tails is trying to "get a reading" on his Miles Electric to help Sonic combat his opponents. Games like Sonic Adventure and even Sonic Battle have shown Tails is completely capable of fighting without the aid of his technology. Yet here, he's seen hiding behind a rock and waiting for his device to get a better signal. This is arguably a dumb mistake on his part simply because of his inaction. While it's possible Sonic would've lost anyway, it's jarring to see Tails on the sidelines while his best friend is getting tossed around.

There's another scene where Tails laments that he wasn't "smart enough" to fix E-123 Omega, and the fake Chaos sneaks up on him. Rather than fight, he ducks his head and calls out for Sonic. Luckily, Classic Sonic rushes to the rescue, but why wouldn't Tails, one of the smartest characters, not think to be more aware of his surroundings or at least try and fight?

3 Sonic Lost World: Being Petty With Eggman

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In any other situation, Tails has every right not to trust Eggman. They've been constantly butting heads since the beginning, but they knew when to put aside their differences when a larger threat entered the scene. In Sonic Lost World, Tails becomes bitter that Sonic's working with Eggman to stop the Zeti. There's a scene where Tails snaps, accusing Sonic of not trusting him in shutting down Eggman's machine. Some fans thought this entire confrontation was out of place and, more importantly, out of character for Tails. Instead of cooperating with Eggman like Sonic, he's constantly dishing out insults at Eggman's tinkering skills whenever they're in a scene together.

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Tails being petty is dumb because it serves no purpose. At this point, he's just being difficult for the sake of conflict and even borders on being ungrateful when Eggman saves him from Cubot. Tails doesn't have to like working with Eggman, but even he knew not to pick fights when Team Sonic had a bigger problem than Eggman on their hands. By the end of Lost World, Tails' attitude serves as an "I told you so" to Sonic, who apologizes for "ever doubting him [Tails]." However, it wasn't that Sonic doubted him, but rather the machine was programmed by Eggman, meaning it would make sense that Eggman would know how to stop it.

2 Sonic Chronicles: Trusting Eggman

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In contrast, Sonic Chronicles does the opposite of Sonic Lost World by having Tails and co. be too trusting of Dr. Eggman. At the start of Sonic Chronicles, Eggman has gone missing since Team Sonic destroyed his base. It turns out Eggman was alive this whole time and that the Nocturnus Clan was controlling his SWATbots - not Eggman himself. For a while, Team Sonic allies themselves with Eggman, and when the Master Emerald is stolen by the Nocturnus Clan, they need to travel between dimensions to get it back. This leads to Sonic and the others using the Blue Cyclone for interdimensional travel, and Eggman stays behind so that there would be someone to pull them back to their world if necessary.

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To no one's surprise, Eggman ends up backstabbing them when they return from the Twilight Cage, having constructed a new Eggman Land during Team Sonic's absence. While it wasn't necessarily only Tails' fault for trusting Eggman (Sonic is just as much to blame), it's still an out-of-character decision on his part. Because while Team Sonic has worked with Eggman in the past, they wouldn't be so foolish as to leave him without surveillance while they were gone. At least Tails isn't throwing insults this time.

1 Sonic Adventure 2: The Fake Emerald

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Another dumb thing Tails has done was accidentally telling Eggman about the fake emerald in Sonic Adventure 2. For context, Tails constructed a fake Chaos Emerald for Sonic to throw into the Eclipse Cannon and cause it to blow up, thwarting Eggman's plans. However, Eggman manages to take Amy hostage, putting him and Tails in a bind. When Sonic arrives on the scene, Eggman traps him and manages to trick Tails into revealing that the emerald Sonic was going to give Eggman was a fake.

This is less of a questionably dumb moment and more of an example of how cunning Eggman can be. Despite this, Tails' slip up allowed Eggman to eject Sonic into space, which would've killed the blue blur had he not tried using Chaos Control. For what it's worth, Tails' plan involving the fake emerald was clever itself, and would have succeeded had things gone differently.

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