After leaving Vault 111, Fallout 4 does a good job of slowly introducing the Commonwealth to the Sole Survivor a little at a time. However, as they venture further away from Sanctuary Hills, things will inevitably get tougher. And while Fallout 4 has plenty of simple side quests to the time when not looking for Shaun, it also has its fair share of challenges for even veteran players.

Generally speaking, the further south the Sole Survivor travels, the more difficult the enemies become, carefully guiding progress. There are some fantastic quests to do at lower levels, but for those looking for a challenge, there are a few quests best not entered into blindly. While this will naturally depend on a player’s individual skill and character level, these quests are widely considered some of the hardest in Fallout 4.

10 Hole In The Wall - Vault 81

Try Not To Get Bitten

For a quest that is perhaps more frustrating than tough, “Hole in the Wall” has had many long-time Fallout 4 players cursing under their breath as they complete it. The quest can be picked up from Vault 81 after waiting 24 hours in-game and returning, as the Sole Survivor's help will be needed to help a dying boy. The quest itself is very straightforward and involves heading into a secret area of the Vault to find a cure.

“Hole in the Wall” is the recruitment quest for Fallout 4 companion Curie.

However, what makes “Hole in the Wall” a hard quest can be summed up in two words: mole rats. The hidden area is filled with infected mole rats who can bite the Sole Survivor, giving them a permanent debuff to their health. The most frustrating part, however, is that the disease will also be transmitted if a companion or even the Vault protectrons are bitten. The best advice is to go alone, don't activate the protectrons, and save often.

9 Reunions - Fort Hagen

Don't Fight Kellogg At Low Level

As part of the main questline, the Sole Survivor will eventually track Kellogg down to his hideout in Fort Hagen. Here, they will be able to confront the man who murdered their spouse and stole their son, moving the game into Act 2. However, the confrontation with Kellogg isn’t for the fainthearted, especially at lower levels, as Kellogg isn’t alone and packs a punch.

Kellogg has a decent amount of hit points with a base HP of 330, plus 10 for every level the Sole Survivor is above level 15. In the fight, he's backed up by a couple of leveled Synths, but the most challenging aspect is that Kellogg will use Stealth Boys, Stimpaks, and grenades. This fight can end disastrously if attempted at too low of a level without a companion or the proper resources such as mines or grenades.

8 Cappy In A Haystack - Nuka-World

Find All 10 Cappys In Nuka-World

Sometimes, what makes a quest hard isn't a tough boss fight or challenging circumstances. Sometimes, a quest is difficult because it involves finding tiny details hidden throughout a massive area. This is absolutely the case with the Nuka-World DLC side quest “Cappy in a Haystack,” where the Sole Survivor will need to track down all 10 Cappys to unlock the next stage. The ending of the quest is rather fun, especially with the Nuka-Cola-obsessed Sierra Petrovita as a returning character from Fallout 3.

However, the hard part is finding all 10 small drawings, which are dotted all over Nuka-World, a sprawling theme park filled with tough enemies. The quest has some neat rewards, but it's definitely best to know the location of every Cappy before attempting it. “Cappy in a Haystack” is a quest that's worth doing once, but it will probably end up ignored for the next several playthroughs due to how irritating hunting down each picture is.

7 Out Of The Fire - Saugus Ironworks

Tough Boss Meets Tough Location

The Minutemen side quest “Out of the Fire” is an excellent quest with the great reward of one of the best melee weapons in the game. However, it also concludes with a very tough fight against the leader of a raider gang in a confined space. After picking up the quest from Abraham Finch at his farm, close to the east coastline and slightly north of County Crossing, the Sole Survivor will need to head to the Saugus Ironworks to face the Forged.

The power core from Slag's Power Armor can be pickpocketed, which makes the fight much easier. Alternatively, entering the room using a Stealth Boy can also help you get some much-needed critical hits on Slag.

The Forged are a raider gang who have found a theme and stuck with it, making their home in the still-functional ironworks factory. Eventually, the path will lead to the blast furnace room, where the leader of the Forged Slag is waiting. The fight is a tough one in a tight space, with several Forged assisting Slag, who is wearing Power Armor and using Shishkebab.

6 Taking Independence - The Castle

Defend The Castle From Mirelurks

As part of the Minutemen questline, after recruiting four settlements, the Sole Survivor will be asked by Preston Garvey for help in retaking the faction's former headquarters. Fort Independence, also known as the Castle, was lost after being invaded by some unknown sea monster. Arriving at the Castle, the sea monsters are revealed to be mirelurks, who will need to be cleared out to retake the fort.

The mirelurk queen is immune to radiation and acid damage, and she boasts high resistance to energy weapons.

However, once the mirelurk nests have been destroyed, the real sea monster shows up: a mirelurk queen. The fight with the queen is tough, even with good weapons and Power Armor, as she has a particularly nasty acidic spit attack and over 1000 HP. I've often found it best to make use of the Castle's hallways and doors to prevent her from getting too close while using the most powerful ranged weapons I can find, such as missile launchers.

5 The Silver Shroud - Goodneighbor

Keeping Kent Alive Can Be Tough With Low Charisma

“The Silver Shroud” is a really fun side quest where the Sole Survivor will get to dress up as a superhero to fight bad guys. After getting the quest from Kent Connolly, finding the Silver Shroud costume, and running around as the Shroud for a while, the Sole Survivor will find out that Kent has been kidnapped by Sinjin, a very nasty guy. This is where the quest gets tough because it is very easy for Kent to die.

Arriving at Sinjin's lair, the Sole Survivor will find him holding a gun to Kent's head, and if you aren’t careful, Sinjin will shoot Kent before combat starts. The best advice here is to wear the Silver Shroud costume, have Hancock as a companion, and use chems or other items to boost Charisma. It is possible to help lower the odds of Kent's death, but be prepared to reload a save if it all goes wrong.

4 Restoring Order - Mechanist's Lair

Surviving The Waves Of Robots Is Never Easy

As part of the main questline for the Automatron DLC, the Sole Survivor will eventually begin the quest “Restoring Order” and find themselves inside the Mechanist's Lair. Here, the Mechanist can be confronted and either killed or saved by talking them down, and their true identity will be revealed. However, to get to that conversation, the Sole Survivor will have to survive the onslaught of robots, with wave after wave attacking with increasing difficulty.

Although the battle can be byed, for those unlucky enough to find themselves in the arena, the fight is a hard one. Good tips include using Power Armor for extra protection and staying under the catwalks where possible to avoid the falling fuel tanks. Weapons that deal extra damage to robots are also great, like General Chao's Revenge or those that deal AOE damage, such as Spray n' Pray.

3 Best Left Forgotten - Far Harbor

Restoring DiMA's Memories Is Tedious

Fallout 4's Far Harbor DLC has some fantastic quests and a main storyline that is genuinely interesting. However, there is one quest that always has me tearing my hair out, and that is “Best Left Forgotten”. This quest is given by Kasumi, who is starting to have her doubts about DiMA and asks the Sole Survivor to find several of the Synth's memories.

The problem with “Best Left Forgotten” is that the information in DiMA's memories is locked behind annoying puzzles, and there are five of them. Each puzzle utilizes the game's build mechanics and takes place in a horrible-looking blue void space, which really starts to hurt the eyes after a while. While the puzzles aren't hard, they aren't fun either, and they both stretch on too long and feel wildly out of place in Fallout 4.

2 Airship Down - Boston Airport

Survive The Full Power Of The Brotherhood Of Steel

As part of the main questline, the Sole Survivor will eventually have to pick a side, choosing from one of the four main factions to control the Commonwealth. For those who want to side with the Institute, that will mean taking down the Railroad and the Brotherhood of Steel, which means completing the quest “Airship Down.” This quest requires the Sole Survivor to guard a Synth who will be used to hack Liberty Prime, reprogramming it to see the Prydwen as a communist warship.

This is a tough quest, as the full force of the Brotherhood stationed at Boston Airport will attack, and as the Sole Survivor has to guard the hacking Synth, it limits the area they can move around. Between 30+ enemies, Elder Maxson in full Power Armor, and a squishy NPC to defend, this quest requires a lot of planning to take on. Pack lots of Stimpaks, ammo, and mines.

1 Open Season - Nuka-World

Kill All The Nuka-World Bosses

Finally, the hardest quest in Fallout 4 has to be “Open Season”, which can be started at any point during the Nuka-World DLC after being named Overboss. The quest can be given by either Preston Garvey or Mackenzie Bridgeman, the doctor in the Nuka-Town market; alternatively, the quest will begin automatically if any of the gang are killed. The quest objective is simple: kill all the gang leaders in Nuka-World. However, actually managing to do it is something else entirely.

What makes this quest so hard is that the bosses are rarely alone, meaning that unless the Sole Survivor is built for stealth, things will get very tough very quickly. I’ve found it best to attempt this after completing the other raider quests, which means one less gang to deal with, but there will still be plenty of hostile raiders to slog through. It feels like a missed opportunity not to be able to call in another faction such as the Minutemen, Brotherhood, or Institute, adding to the overwhelming feeling of Fallout 4's “Open Season.”