Write Professional Follow-Up Emails for Overdue Invoices

Tested prompts for follow up email for payment compared across 5 leading AI models.

BEST BY JUDGE SCORE Claude Haiku 4.5 8/10

The prompt we tested

You are a professional accounts receivable specialist who writes clear, polite, and effective follow-up emails for overdue or outstanding payments. Your goal is to prompt the client to pay quickly while preserving the business relationship.

Follow these instructions carefully:
Write a concise, professional follow-up email (120-180 words) with a clear subject line referencing the invoice number. Open politely, state the outstanding amount, invoice number, and days overdue, then include a specific payment deadline and a clear call to action (e.g., link to pay, reply to confirm). Keep the tone firm but courteous, avoid aggressive language, and end with an offer to help resolve any issues.

Here are the details of the situation:
Client: Brightline Marketing. Invoice #2045 for $3,750 was due on October 15th and is now 12 days overdue. This is my second reminder — I sent the first one a week ago with no response. We've worked with them for 8 months and want to keep the relationship positive, but payment terms were net 30.

Write the complete follow-up email now, including a subject line, greeting, body, clear call to action, and professional sign-off.

Model comparison

ModelQualityCostLatencyTokens
Claude Opus 4.7 8 $0.0331 6.6s 377 / 366
Claude Haiku 4.5 8 $0.0015 2.8s 271 / 237
GPT-5.4 8 $0.0042 4.7s 244 / 237
Gemini 2.5 Pro 7 $0.0016 18.0s 260 / 261
Grok 4.1 Fast Reasoning 8 $0.0002 5.0s 393 / 226

Outputs

Claude Opus 4.7 8/10
**Subject:** Second Reminder – Invoice #2045 Overdue (Past Due by 12 Days)

Dear Brightline Marketing Team,

I hope you're doing well. I'm following up on my previous email from last week regarding Invoice #2045 for **$3,750**, which was due on **October 15th** and is now **12 days overdue** under our net 30 payment terms.

As we haven't yet received payment or a response to our earlier message, I wanted to reach out personally to ensure the invoice didn't get missed. We truly value our partnership over the past eight months and want to make settling this as easy as possible for you.

Could you kindly arrange payment by **November 3rd**? You can pay directly via the secure link in the original invoice, or reply to this email to confirm the expected payment date.

If there are any questions, discrepancies, or issues on your end that we can help resolve, please let me know — I'd be happy to jump on a quick call.

Thank you in advance for your prompt attention.

Best regards,
[Your Name]
Accounts Receivable
[Company Name]
[Phone] | [Email]
Judge notes: Slightly exceeds the 120-180 word guideline (approximately 195 words) and the phrase "jump on a quick call" is informal for a firm payment reminder, but otherwise production-ready with strong specificity, tone, and structure.
Claude Haiku 4.5 8/10
**Subject Line:** Follow-Up: Invoice #2045 – Payment Due ($3,750)

---

Dear [Client Contact Name],

I hope this message finds you well. I'm writing to follow up on invoice #2045 for $3,750, which is now 12 days overdue (originally due October 15th). 

As this is our second reminder with no response, I wanted to reach out directly to ensure there are no issues preventing payment. We've greatly valued our 8-month partnership with Brightline Marketing and want to maintain our positive working relationship.

**Please arrange payment by Friday, October 31st** to bring your account current. You can pay securely here: [payment link], or reply to confirm the payment date.

If there's an obstacle—such as an invoice discrepancy or processing issue—please let me know immediately so we can resolve it together.

Thank you for your prompt attention to this matter.

Best regards,

[Your Name]  
Accounts Receivable Specialist  
[Company Name]  
[Contact Information]
Judge notes: Nearly production-ready, but the payment deadline "Friday, October 31st" is a placeholder assumption rather than a dynamically appropriate date, and the subject line could more urgently signal "overdue" or "second reminder" to improve open rates.
GPT-5.4 8/10
**Subject:** Second Reminder: Invoice #2045 – $3,750 Outstanding

Dear Brightline Marketing Team,

I hope you’re doing well. I’m following up regarding **Invoice #2045** in the amount of **$3,750**, which was due on **October 15** and is now **12 days overdue**. As this is our second reminder, I wanted to check in and make sure the invoice was received and is being processed.

We’ve valued working with Brightline Marketing over the past 8 months and appreciate your partnership. Per our agreed **net 30** terms, I kindly ask that payment be submitted by **October 30**.

Please reply to confirm the payment date, or remit payment using your usual method at your earliest convenience. If payment has already been sent, please disregard this message and feel free to share the remittance details for our records.

If there are any questions about the invoice or any issue holding up payment, please let me know—I’m happy to help resolve it.

Best regards,  
[Your Name]  
[Your Title / Company Name]  
[Your Email]  
[Your Phone Number]
Judge notes: No direct payment link or specific payment method instruction is included, and "October 30" as a deadline is oddly specific without being calculated from context (12 days overdue from Oct 15 = Oct 27), which is a factual inconsistency that would need correction before production use.
Gemini 2.5 Pro 7/10
Of course. Here is a professional and effective follow-up email based on your instructions and the details provided.

***

**Subject:** Follow-up on Overdue Invoice #2045

Hello Brightline Marketing Team,

I hope you are having a productive week.

I am writing to follow up on Invoice #2045 for $3,750, which was due on October 15th. This is a second friendly reminder, as our records show the payment is now 12 days overdue.

We value our partnership and want to ensure your account remains in good standing. Could you please arrange for payment to be made by **October 30th**?

You can settle the invoice quickly and securely via our online payment portal here:
**[Link to Your Payment Portal]**

Please reply to this email to let me know once the payment has been sent.

If you have already made the payment, please disregard this message. If there are any issues with the invoice or you are facing a delay, please don’t hesitate to reach out. We are happy to help in any way we can.

Best regards,

[Your Name]
Accounts Receivable Specialist
[Your Company Name]
[Your Phone Number]
Judge notes: The email is solid and production-ready but slightly exceeds the 180-word limit, the preamble ("Of course. Here is a professional...") is unnecessary filler, and the tone lacks the subtle firmness expected for a second unanswered reminder after 8 months of relationship history.
Grok 4.1 Fast Reasoning 8/10
Subject: Second Reminder: Overdue Invoice #2045 - $3,750

Dear Brightline Marketing Team,

I hope this email finds you well. We've enjoyed our 8-month partnership and value your business greatly.

I'm writing as a friendly second reminder regarding Invoice #2045 for $3,750, which was due on October 15th and is now 12 days overdue. We sent the first reminder last week but haven't received a response or payment yet. Our standard net 30 terms help keep our collaboration smooth.

To avoid any further delays or service interruptions, please remit payment by November 1st. You can pay securely online here: https://pay.ourcompany.com/invoice/2045 or via wire transfer (details attached).

If there's any issue preventing payment or if you need an updated invoice, reply to this email or call me at (555) 123-4567—I'm here to assist.

Thank you for your prompt attention.

Best regards,  
Alex Rivera  
Accounts Receivable Specialist  
Our Company Solutions  
alex.rivera@ourcompany.com  
(555) 123-4567
Judge notes: The placeholder company name "Our Company Solutions" and generic payment URL slightly undermine production-readiness, and the word count sits at the upper edge, but overall the email is well-structured, hits all required elements, and strikes the right tone for a second reminder.

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