• Be specific with dates, amounts, and deliverables
• Reference your contract sections where possible
• Stick to verifiable facts, not opinions or character attacks
• Keep the tone professional and businesslike
• Set a realistic deadline (10-14 days is standard)
• State consequences if ignored, but don't make empty threats
• Offer a reasonable path to resolution
• Send to the highest-ranking person you can identify

Situation: You paid a marketing agency $20,000 to run a Q4 holiday campaign. They missed the launch deadline, delivered unusable creative assets, and stopped responding to emails.

Key Points to Include:

• Specific campaign launch date from contract
• List of deliverables promised vs. what was delivered
• Timeline of missed deadlines and communications
• Lost opportunity costs (missing holiday shopping season)
• Screenshots of unusable creative work

Typical Demand: Full refund of $20,000 plus reimbursement for replacement agency costs, plus demand for immediate transfer of ad account access and any completed materials.

Situation: A development shop was paid $40,000 to build a custom web application by November 1st. The delivered application crashes frequently, fails security tests, and is missing key features from the spec.

Key Points to Include:

• Reference technical specifications from Statement of Work
• Detailed bug reports and test results
• List of missing features with contract references
• Security vulnerabilities discovered
• Business impact of unusable application

Typical Demand: Either (1) completion of work to specifications within 30 days at no additional cost, with right to inspect and test, OR (2) refund of $40,000 plus immediate transfer of all source code and credentials.

Situation: You paid a business consultant a $15,000 retainer for strategic advisory services including weekly calls and monthly reports. After an initial call, the consultant ghosted you.

Key Points to Include:

• Contract terms specifying hours or deliverables
• Timeline of your attempts to reach them (with dates)
• Lack of any substantive work performed
• Simple calculation: $15,000 paid - minimal work = unjust enrichment

Typical Demand: Full refund of $15,000 less any hours actually worked (typically none or minimal), with detailed accounting if they claim they did work.

Don't explicitly condition silence about alleged crimes on payment:

• "Pay me $20,000 or I'll report you to the IRS for tax fraud"
• "Settle by Friday or I'm filing criminal fraud charges with the DA"
• "Give me my money back or I'll report you to your licensing board and destroy your career"

Don't threaten a social media smear campaign for payment:

• "Pay up or I'll post about this scam on every review site and social media platform"
• "Settle this or I'm starting a viral campaign to expose your fraud"

Why this is illegal: California Penal Code §518 makes it extortion to obtain property through wrongful use of force or fear. The landmark case Flatley v. Mauro (2006) held that an attorney's demand letter threatening to report alleged rape to authorities unless the target paid was criminal extortion, not protected legal activity.

You CAN state you'll pursue civil remedies:

• "If we cannot resolve this informally, I will pursue all appropriate civil remedies, including filing a breach of contract claim in [court/arbitration]"
• "I am prepared to initiate litigation to enforce my contractual rights if this is not resolved by the deadline"
• "Under our Agreement, the prevailing party is entitled to attorney's fees, which I will seek if legal action becomes necessary"

You CAN mention regulatory complaints separately from payment demands:

• "This letter addresses civil contractual claims only. Separate from this demand, I am evaluating whether your conduct warrants complaints to [relevant regulatory body], which I may pursue independently"
• "I reserve the right to file appropriate complaints with regulatory agencies regarding your business practices"

Factual and Safe:

• "You received payment of $15,000 on August 1, 2025, but have not delivered the contracted services as of November 19, 2025"
• "The application crashes when processing payments, as documented in the attached error logs"
• "Despite my emails on [dates], you have not responded"

Potentially Defamatory:

• "You are a scam artist who deliberately defrauds clients"
• "Your company is a criminal enterprise"
• "You have a history of ripping people off"

The Rule: Stick to verifiable facts you can prove with documentation. Avoid character attacks, speculation about intent, or sweeping accusations. Use neutral framing: "Our records show..." "According to the attached invoices..." "The evidence indicates..."

Even when you're furious (and rightfully so), keep the letter businesslike. Emotional, insulting, or threatening language:

• Weakens your legal position
• Can create defamation or harassment claims against you
• Makes settlement less likely (vendors dig in when attacked)
• Looks bad if a judge or arbitrator later reads it

Remember: The goal is to get paid or get your work completed, not to "win" an argument or punish the vendor. A professional, fact-based letter that offers a reasonable resolution is far more effective than an angry rant.