Every business owes tax somewhere, and the exposure rarely sits in one place. Income tax filings, payroll withholding, state and sales tax, and the entity structure the company chose years ago all create obligations that can turn into a dispute.
Whiteford represents companies of every size, from a first-year startup to an established multistate operation. The work runs from choosing and maintaining an entity structure, through planning for changing tax rules, to defending the company when the IRS or a state tax authority questions a return.
When a dispute does arrive, the sequence matters. Getting representation in place early keeps an IRS audit inside its original scope, preserves privileged communications, and keeps a civil examination from drifting toward allegations of wrongdoing.
Where business tax exposure becomes personal
Payroll tax is the clearest example. Amounts withheld from employee wages are trust fund money, and when they are not paid over the IRS can assess the Trust Fund Recovery Penalty against the owners, officers, or managers it identifies as responsible persons. The company's problem becomes a personal one, collectible from personal accounts and property.
Common issues
Entity structure and tax planning
The structure a company files under drives its tax treatment, and the choice made at formation is rarely revisited as the business grows. We advise on structure and on planning for changing tax rules, so the position the company reports is one it can defend later.
Payroll taxes and the Trust Fund Recovery Penalty
Withheld Social Security and Medicare are trust fund money held for the government. If they are not paid over, the IRS can assess the penalty personally against owners, officers, and anyone else with control over which bills get paid, then levy their accounts and lien their property.
IRS audits of a business return
Most audits begin with a letter asking for proof of something the return reported. What the company hands over in the first weeks decides whether the examination stays narrow or expands into more years and more issues. We act as the point of contact and keep it in scope.
Delinquent filings and unpaid balances
Missed Forms 941, 940, 1120, or 1065, along with state sales and use tax returns, create two separate problems: the filing gap and the balance. They carry different deadlines, and the order in which they are addressed changes what relief is available.
State and local tax
Businesses pay income tax at the state level as well as the federal, plus payroll tax and sales tax on what they sell. State audits look back three years or more and ask for W-2s, 1099s, receipts, bills, and canceled checks. We handle those examinations and the appeals that follow.
Privilege and allegations of wrongdoing
Communications with a lawyer carry protection that communications with an accountant do not. When an examination starts probing intent rather than numbers, or a PPP or ERC claim is in question, that difference decides what can safely be put in writing and by whom.
Recommended next steps
- Route the examiner's requests through counsel before the company answers them.
- Confirm which payroll, income, and sales tax filings are actually missing before you file anything.
- Identify everyone who decides which bills get paid, because those are the people the IRS will name as responsible persons.
- Keep sensitive analysis in a privileged channel rather than in email to the bookkeeper.
How we help
Frequently asked questions
When does a business need a tax attorney rather than its accountant?
Can the IRS collect the company's payroll taxes from me personally?
The business has years of unfiled returns. Where do we start?
What does an audit of a business return usually focus on?
Where we work
All Whiteford offices where you can meet with an attorney
Baltimore
Suite 1500
Baltimore, MD 21202
Columbia
Suite 400
Columbia, MD 21045
Ocean City
Ocean City, MD 21842
Rockville
Suite 800
Rockville, MD 20850
Towson
One West Pennsylvania Avenue
Towson, MD 21204-5025
Denver
Denver, CO 80211
Bethany Beach
Bethany Beach, DE 19930
Rehoboth Beach
Rehoboth Beach, DE 19971
Wilmington
Suite 300
Wilmington, DE 19801
Washington, DC
Suite 1300
Washington, DC 20006
West Palm Beach
West Palm Beach, FL 33401
Lexington
Lexington, KY 40507
Fairfield
Suite 100
Fairfield, NJ 07004
New York
4th Floor
New York, NY 10022
White Plains
White Plains, NY 10604
Charlotte
Suite 315
Charlotte, NC 28211
Pittsburgh
Suite 1400
Pittsburgh, PA 15222
Falls Church
Suite 800
Falls Church, VA 22042
Richmond
Suite 2001
Richmond, VA 23219
Roanoke
Suite 1110
Roanoke, VA 24011
Virginia Beach
Suite 300-91
Virginia Beach, VA 23462
No offices in that state yet. Federal matters are handled from any office.