I have been both player and DM when this problem has surfaced. Sometimes it is something as simple as the DM being afraid to let any PCs die, or suffer significant setbacks after failing an encounter. It's nice that the DM is worried about their players and player characters, but there needs to be a balance. Somewhere between the antagonistic and apathetic "Killer DM" who seeks the destruction of the players, and the friendly game-runner who just wants to see his players win all the time lies a happy medium.
If your game is too easy, you will start to see symptoms soon enough. Players will start to actively pursue more difficult encounters and challenges in an attempt to test out the difficulty of the campaign. If they are consistently successful and impervious to any major consequences, then you risk boredom and the stagnation of your gaming sessions.
Oddly enough, some players may also begin to get increasingly paranoid about failing the simplest of tasks. This is why you want to show your players that they can overcome setbacks when they happen. You want your players to want to avoid negative consequences but accept them when they occur. Don't make your players afraid of failure. If a die roll goes badly and you soften or refuse to recognize the bad result, it's going to do just that. It's going to make the players feel like the consequences are so bad that even the DM doesn't want to administer them. Like an over-protecting parent, you make the PC afraid of the world around them. It's an unhealthy attitude that leads to either a lack of challenge in your games or a crippling sense of fear and reluctance to act from your players.
If the players accomplish every single thing they set out to do, it's not a game. It's not even a story. Stories require conflict. They require obstacles to interact with and overcome. The enjoyment we get from achievement comes from the fact that it is earned through persistence. Make each die roll count, remember to only roll when it really matters. Let there be truly compelling challenges and consequences in your campaigns. Let the players struggle and fight for their victories. Don't abuse them, but encourage them to stand up to the obstacles you present them with and find their triumph. You want an environment in which it isn't always easy to win, but it's possible and surmountable. There's no real satisfaction in a victory unearned, so make the challenge fit the reward. Then you can have truly satisfying moments for your gaming group, and fun stories that can be remembered and retold for days to come.
Happy ventures!
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