Short answer: the contractor is usually the one on the hook. Hiring an independent contractor to do a common-element repair, a roof, sidewalks, siding, generally does not make the HOA vicariously liable for the contractor's mistakes. The HOA only becomes liable through its own fault: if it negligently hired an unfit contractor, kept control of how the work was done, or the job was inherently dangerous. So your first target is the contractor's insurer, with the association's policy and its statutory repair duty behind it.
Is the HOA responsible for its contractor's mistakes?
Usually not, by default. This is the long-settled "independent-contractor rule." An Illinois appellate court stated it cleanly in a case with almost exactly these facts, a homeowners association hired a contractor to repair common-element sidewalks and a resident sued the association:
"One who employs an independent contractor is not liable for the latter's acts or omissions [citations] except where the principal orders or directs the acts causing the harm, negligently selects an incompetent contractor [citation], or retains control over the 'operative details of the contractor's work.'"
DiMaggio v. Crossings Homeowners Ass'n, 219 Ill. App. 3d 1084 (1991)
California's Supreme Court says the same, and it is the majority rule nationwide (courts trace it to Restatement (Second) of Torts §409):
"At common law, a person who hired an independent contractor generally was not liable to third parties for injuries caused by the contractor's negligence in performing the work."
Privette v. Superior Court, 5 Cal. 4th 689 (1993)
So the fact that "the HOA hired the guy" is, by itself, not enough to make the HOA pay for your damaged unit.
When IS the HOA on the hook?
Through its own negligence, in one of these situations:
- Negligent hiring/selection. The board hired a contractor it knew, or should have known, was unfit. Per DiMaggio: the owner "would be required to show that defendant negligently hired an independent contractor which it knew, or should have known, was unfit for the job so as to create a danger of harm to plaintiff."
- Retained control. The board or management company didn't just hire and step back, it directed the operative details of the work, or ordered the specific act that caused the damage (also from the DiMaggio rule above).
- Inherently dangerous ("peculiar risk") work. A real, if narrower, exception: if the work carries a special danger to neighboring property, the hiring party can be liable even without its own fault. Privette confirms this exception historically reached "innocent bystanders or neighboring property owners who were injured by the negligent acts of an independent contractor hired by the landowner to perform dangerous work", the posture closest to a damaged neighboring unit.
- Non-delegable duty. Some duties (like an association's duty to keep common areas reasonably safe) can't be contracted away, the association keeps ultimate responsibility even after hiring someone to do the work.
Who do I file a claim against first?
- The contractor's commercial general liability (CGL) insurance. The contractor caused the damage and is the primary target, ask for their certificate of insurance and put their carrier on notice.
- The association's own insurance and repair duty. In many states the association must insure and reconstruct common-element property regardless of fault (below), and its general-liability policy may respond.
- A direct negligence claim against the HOA, but only if one of the exceptions above actually applies and you can prove it.
Does the association's insurance cover it?
Often there's a statutory backstop independent of who is "at fault." Florida is explicit that the association must insure and rebuild the insured common-element property:
"Any portion of the condominium property that must be insured by the association against property loss pursuant to paragraph (f) which is damaged by an insurable event shall be reconstructed, repaired, or replaced as necessary by the association as a common expense."
Fla. Stat. §718.111(11)
And the reason the association is the one hiring the contractor in the first place is that the common area is its responsibility, e.g., California's Davis-Stirling Act: "the association is responsible for repairing, replacing, and maintaining the common area" (Cal. Civ. Code §4775). That duty is a lever: the association can't escape its obligation to restore common-element property just because a contractor it chose did the damage.
The honest caveat
This is highly state- and fact-specific, and not legal advice. Negligent-hiring, retained-control, and "peculiar risk"/non-delegable-duty doctrines vary considerably by state and turn on the facts, what the board knew about the contractor, how dangerous the work was, who controlled the jobsite, and what your declaration and the association's certificate of insurance actually say. Read your declaration and the association's insurance certificate, document everything, and talk to a local real-estate or tort attorney before assuming any of the above applies to you.
Related, on the cost-allocation side (as opposed to this negligence question): who pays for repairs in an HOA or condo, and who pays after a condo water leak in Florida. Look up your city at the city lookup or browse all guides.