Saber I was wondering if you could recommend some whump Tony fics a long the lines of kiyaar’s Sins of Omission, MissBecky’s Captivated or the more recent When Sorrows Come by Ironlawyer.You know the kind where he’s broken and hurting, but still trying to do his best…

Those are all great fics.  You should check out the Whump!Tony list, but here are a few other Dark Fic suggestions for you. I think what the ones you mentioned have in common is not just Tony trying, but things not always wrapping up so rainbows and unicorns at the end.  I’ll include the with the ones you already suggested for others who  might be interested in reading them.  You might notice some repeated names on the list, and I always suggest if you like a fic by an author, check out their author page for more.

DON’T LEAVE YOUR AUTHORS BROKEN AND HURTING WITHOUT COMMENTS AND KUDOS! WE ARE DOING OUR BEST!

When Sorrows Come by @ironlawyer: When Tony gets captured by a sadistic alien who takes a
shine to him, hurt and alone, he must deal with a ruthless tormenter as
well as his guilt, fear and addiction.When he finally makes it
out alive, he is a physical and emotional mess and must face the
temptation to use alcohol to quiet his demons whilst rebuilding his
home, his relationships and himself.

The Illusion Cannot Be Sustained by @ironlawyer​:
When Tony first decided liquor was more important than pride, he
promised himself one thing – blowjobs only. But when a man who looks too
much like Steve comes along, that’s all about to change.

Thirty Pieces of Silver by FluffyPanda:
Tony Stark has betrayed the Ultimates and nothing is what Steve thought it was.

All Time Low by @sineala:
Tony’s lost his company to Obadiah Stane. He’s lost it all: his money,
his friends, his Avengers team… and his sobriety. Drunk, homeless,
Tony is living on the streets, and when he runs out of liquor money, he
sells the only thing he has left: his body. And one day, he has the
exact wrong customer.

voglio sentirti by lackluster_lexicon:
Steve returns to Stark Tower ten months after leaving Tony in Siberia.

To the Victor by @thegraytigress: Nightmares are real.  Tony is living one.  It’s awful,
unending, torturous.  It’s driving him mad.  It’s killing him.  He just
wants to wake up and go back to his life with Steve, a life filled with
love and happiness. Yet every day the hell of reality presses down,
because Steve went on a mission. Steve made the ultimate sacrifice.
Steve is never coming home. And Tony can’t let himself believe it.

Resistance by @thegraytigress (WiP): After being kidnapped during a fight, Tony and Steve
find themselves in a nightmare unlike any other.  They’re millions of
miles from home and trapped in an alien labor camp that can only be
described as hell.  There’s no chance of being found, no hope of being
rescued, and they’re facing deplorable conditions, vicious guards, and
other prisoners who are sadistic and cruel and just desperate to prey on
them.  Again and again they’re told they only have two choices in this
place: work or die.They choose something else.  Survival.

The Silence In Between by @winterstar95: Steve Rogers put the Red Skull’s plane filled with
bombs that could end civilization into the Arctic Ocean at the cost of
his life. Over seventy years later, he wakes up imprisoned and under the
control of the State, a tyrannical government based on the legacy of
Johann Schmidt and Hydra. With a neural net implanted in his brain to
control his every move, his every thought, Steve Rogers, once Captain
America, is assigned as Primary Designate for one of the Ruling
Families. His duties as Primary Designate include the protection of the
sole remaining heir to Stark Industries, Tony Stark. As bodyguard, Steve
learns that the world is a very different place; not all is as it
seems, and no one can be trusted. His introduction to the 21st century
has just begun but the war against Hydra is everlasting.Warning: Chapters 13-15, 24 will contain graphic depictions of violence and torture.

Sins of Omission by @kiyaar (wip): A Post-Civil War, Pre-Secret Invasion AU where Steve is dead, Tony’s a mess, and everything sucks. In which Tony deals poorly with Steve’s death, falls off the wagon, sees ghosts, and misses a lot. Oh, and the Skrulls are about to invade.

Plunge by @kiyaar:
How the Illuminati ruined everything and no one was able to pick up the pieces.

5, 4, 3, 2, 1 by @kiyaar:
In another world, on another Earth, the Superhuman Civil War has a darker, bloodier end.

Rusted Wheel (or How Civil War Might Have Ended) by @kiyaar:
Tony was on the steps of the Courthouse and took the bullets for Steve.

Our Love is a Ghost that The Others Can’t See by @kiyaar: Post-Civil War, canon-divergent from Director of SHIELD.
In Tony’s dreams, he is back in the street, in a crater, the city
on fire around him. Steve kneels over him and beats him to within an
inch of his life.

It’s his favorite place to be, these days.

won’t let it take you from me by navaan:
Tony is injected with the Zemo formula and things don’t look good, but Steve doesn’t want to give up on him.

Captivated by @missbeckywrites:
When Tony sustains a life-threatening injury, Steve takes him to a world
where magic can heal any wound. But their happy ending swiftly becomes a
nightmare when slavers attack, and Tony is captured and taken away.
After months apart, they are finally reunited, but the quest to save
Tony is only just beginning.

Survival by @missbeckywrites:
Usually it’s just an academic question: how far would you go to survive
in hell? Two years as a prisoner in Jotunheim, and Tony Stark knows
exactly what it takes to stay alive. Even if it costs him his humanity.

Authorization by @missbeckywrites:
Tony always knew JARVIS would turn on him one day. He just didn’t expect it to be today.

The Only Other Sound by @kaesaria:
Hang on, Tony, we’re coming, Steve says, but he doesn’t say it.

If You Love Me by Pearl_Unplanned:
The entire world was a spiral of darkness and despair, choking out any
sort of hope or light that might come across its deadly and destructive
path. Sounded a bit overdramatic, but Tony didn’t care. He’d been called
overdramatic far too many times t really care anymore. In fact, there
was a lot of stuff that he didn’t care about anymore.
–
Tony’s drinking again, post-Ultron, when he decides things might be better if he’s not there anymore. Steve disagrees.