Let’s say you’re sending a demand letter to someone that owes you money. You or your lawyer has written a solid letter, but here’s the thing – even the best-written letter is useless if you can’t prove the other party received it.
That’s why how you send your letter matters as much as what you write in it. In this guide, we’ll walk through your options and figure out what works best for different situations. Feeling overwhelmed by the process of sending a demand letter? Have a lawyer write, sign, and mail a demand letter for you using our flat rate service. Click below to get started.
The Classic Approach: Certified Mail
Remember the last time you had to sign for a package? Certified mail works like that, and it’s still the gold standard for sending demand letters. Here’s what makes it special:
- You get a tracking number
- Someone has to sign for it at the other end
- You get proof of exactly when it was delivered
- Lawyers love it because it creates a clear paper trail
Take Sarah’s case. She runs a small marketing agency and had a client ghost her on a $7,500 project. When the case went to small claims court, Sarah’s certified mail receipt proved exactly when her client received the demand letter. That helped her case, and she was able to win a settlement. However, using certified mail can also have some downsides, which we’ll discuss next.
The Downside of Using Certified Mail
The “Not Home” Game
People can and do avoid certified mail in several ways. Some recipients simply never answer the door when the postal carrier attempts delivery. Here’s how it typically plays out:
- The carrier leaves a notice
- The letter sits at the post office
- After 15 days of no pickup, it gets returned to sender
- The sender has proof of attempted delivery but no actual receipt
Refusing Delivery
Recipients also have the right to refuse certified mail. In fact, many experienced debtors know that certified mail usually means legal trouble, so they simply tell the postal carrier, “I refuse delivery.” The letter then gets marked as “Refused” and returned to the sender.
Take James’s case. He sent a certified demand letter to a former tenant about property damage. The tenant saw the postal carrier coming with certified mail and simply said, “I refuse.” The letter came back marked “Delivery Refused” — technically giving James proof of an attempt, but not actual delivery.
Extra Costs
While a single certified letter isn’t extremely expensive (about $7-8 depending on the service used), costs add up when:
- You need to send multiple letters
- You’re dealing with multiple parties
- Letters get returned and need to be resent
- You add a return receipt service for extra proof
Regular Snail Mail
Sending a demand letter by regular mail is nothing fancy — just add a stamp, and into the mailbox it goes. Some lawyers suggest sending two copies of every demand letter: one certified and one regular.
Why? Because while certified mail gives you better proof of delivery, regular mail is more likely to actually get read. Maria, a freelancer, had success with this approach. Her client never picked up the certified letter from the post office but responded immediately to the regular mail copy.
If you’re thinking about sending a demand letter just using regular mail, there are some major drawbacks. Here are some reasons why you should not use regular mail alone to send a demand letter:
- No Proof of Delivery.
The biggest issue is you have no way to prove the letter was delivered. If the recipient later claims, “I never got your letter,” you have no evidence to counter this claim. This can be particularly problematic if the dispute ends up in court. - No Tracking.
Without tracking, you can’t:- Know if/when the letter arrived
- Prove when you sent it
- Know if it got lost in transit
- Document delivery attempts
- Reliability Issues.
Regular mail can face several problems:- Letters can get lost in the mail
- They might be delivered to the wrong address
- Weather or other issues might delay or damage mail
- Mail can be misplaced or mishandled
- Legal Considerations.
In some situations, regular mail may not satisfy legal requirements:- Some contracts specify delivery methods
- Certain legal notices require traceable delivery
- Some states require proof of delivery for specific types of claims
- Insurance claims might require documented delivery
- Documentation Gaps.
If legal action becomes necessary, you’ll lack:- Proof of mailing date
- Confirmation of delivery
- Evidence of attempted communication
- A paper trail for court proceedings
Special Situations: International and Complex Cases
Sending demand letters across borders? That’s a whole different ballgame. Lisa learned this when she needed to send a demand letter to a supplier in China. International certified mail took three weeks to arrive, and the tracking updates were spotty at best.
For international letters, consider:
- International courier services (like FedEx or DHL)
- Local legal requirements (some countries have specific rules)
- Time zones and delivery times
- Language barriers in confirmation receipts
Making the Right Choice
So, how do you decide which method to use? Think about the following points:
A) Time Sensitivity
If your situation is urgent (like a property damage issue that’s getting worse), use multiple methods. Email gets there instantly, while certified mail creates your legal paper trail. Let’s say you discover your upstairs neighbor’s leaking bathtub is causing water damage to your ceiling. You need them to fix it ASAP before the damage gets worse:
- Send an email immediately with photos
- Follow up with certified mail the same day
- Send regular mail copy as backup
- Keep records of all three methods
This approach gives you:
- Immediate notification (email)
- Legal protection (certified mail)
- Practical backup (regular mail)
- Multiple timestamps of notification
- Various forms of delivery proof
B) Who You’re Dealing With
The type of person or company you’re sending the letter to matters:
- Large companies usually have systems for receiving legal documents
- Individual people might dodge certified mail but read regular mail
- International businesses might prefer digital communication
- Less tech-savvy recipients might not use email frequently
- Home addresses might not be good for certified mail if the recipient works during the day
The Bottom Line
Think of sending a demand letter like backing up your computer — it’s better to be too careful than wish you had been. Using multiple delivery methods might seem overkill, but it’s much better than having someone claim they never got your letter.
The goal isn’t just getting your letter delivered — it’s being able to prove it was delivered if you ever need to. A few extra dollars spent on proper delivery now can save you thousands in legal fees later.