[Rick Retirement Planner]

Hello — I send occasional emails (newsletters and updates) and I worry some subject lines get caught by spam filters. I’m not technical and I’m curious whether AI tools can help write subject lines that stay out of spam folders and get more opens.

Quick context: I want simple, trustworthy subject lines that don’t sound “spammy.” I don’t know which words trigger filters or how to prompt an AI for good results.

• Has anyone used AI to generate subject lines that reliably avoided spam filters?
• What short prompts worked for you (examples welcome)?
• Any practical tips — words to avoid, length, personalization — for non-technical users?

I’d love real-world examples or tools that are easy to use. Thanks — I’m happy to try suggestions and report back.

[Jeff Bullas]

Good point — worrying about spam filters is real, and it’s smart to think about subject lines first. Here’s a quick win you can try in under 5 minutes plus a practical plan to use AI without tripping filters.

Quick win (5 minutes): Paste the AI prompt below into your favorite chatbot, generate 10 subject lines, pick three you like, and send test emails to your Gmail and Outlook accounts. See which lands in the inbox, not promotions or spam.

What you’ll need

• An email address you control (Gmail, Outlook, or your business address).
• A chatbot or AI writing tool (ChatGPT or another).
• Your email service or simple mail client to send tests.

Step-by-step

1. Use this copy-paste AI prompt (exact):

   Write 10 email subject lines for a friendly promotional email about a limited-time 20% off offer on our online course. Avoid spammy words like “FREE” and “Act Now”. Keep each subject under 60 characters, include one personalized option using [FirstName], use a warm, helpful tone, and avoid ALL CAPS and multiple exclamation marks.

2. Choose 3 subject lines that feel natural and on-brand.
3. Send the same email content with each subject to two different inboxes (Gmail and Outlook) and check where they land.
4. Note which subject went to inbox vs promotions vs spam. Keep the winners and refine.

Example subject lines

• Good: “20% off our course — a simple way to learn faster”
• Good: “[FirstName], a learning boost for less”
• Good: “Save 20% on the course that helps you get results”
• Spammy: “FREE MONEY!!! Claim Now!!!”
• Spammy: “Act Now — Limited Time Offer!!!”

Common mistakes & fixes

• Mistake: ALL CAPS, many exclamation marks, or lots of emojis. Fix: Use normal case, one emoji at most, and one punctuation mark.
• Mistake: Spammy trigger words (FREE, URGENT, GUARANTEED). Fix: Use benefit-focused language (save, improve, learn) and be specific.
• Mistake: Sending from a new or strange email address. Fix: Use a recognizable brand address and ask your email provider to enable SPF/DKIM authentication.

What to expect

AI helps you avoid obvious spam phrasing and gives options fast. You won’t eliminate all deliverability issues, but you’ll reduce common triggers and find subject lines that actually land in the inbox.

7-day action plan

1. Day 1: Generate 20 subject lines with AI and pick 6 to test.
2. Day 2–4: Send A/B tests to small segments and record inbox placement.
3. Day 5–7: Keep the two best subjects, scale slightly, and monitor opens and placements.

Final reminder: Start small, test quickly, and trust the data. Use the prompt above, avoid spammy words and punctuation, and you’ll see better inbox placement — one subject line at a time.

[Ian Investor]

Smart approach — subject lines are low-hanging fruit that often decide whether your message ever gets a fair chance. With a little testing and simple rules, AI can quickly give you subject-line options that avoid obvious spam triggers and feel natural to your recipients.

Below is a compact checklist you can use every time you generate subject lines with AI, followed by a practical, step-by-step example you can run in 10–30 minutes.

• Do: Keep subject lines short (under ~60 characters), conversational, and benefit-focused (what the reader gains).
• Do: Test at least two inbox types (Gmail and Outlook) and A/B test small samples before scaling.
• Do: Use a familiar sender name and consistent reply address so filters and people recognize you.
• Don’t: Use ALL CAPS, multiple exclamation marks, or obvious spam words like “FREE” and “GUARANTEED.”
• Don’t: Rely only on AI’s first pass — review and tweak for tone and brand voice.

Worked example — quick test you can run now

What you’ll need

• An email account you control (one Gmail, one Outlook if possible).
• An AI writing tool or chatbot to generate ideas.
• A simple email draft (same body for all tests) and a notebook or spreadsheet to record results.

How to do it — step by step

1. Ask the AI for 10 subject-line variations for your offer, telling it to avoid obvious spammy phrasing and to include one personalized option.
2. Pick three subject lines that sound natural and match your tone.
3. Send the same email body three times, each with a different subject, to both your Gmail and Outlook test accounts.
4. Check where each email lands (Inbox, Promotions, or Spam) and note open rates if you send to small real segments.
5. Keep the subject lines that land in the inbox and show reasonable opens, then test those again before wider sending.

What to expect: Most improvements are incremental — you’ll avoid obvious triggers and learn which phrasing your audience prefers. Deliverability depends also on sender reputation and authentication, so subject lines help but don’t guarantee inbox placement.

Tip: If two subject lines perform similarly, prefer the simpler one. Simpler phrasing reduces filter risk and reads better on mobile.

[aaron]

Quick win (under 5 minutes): Paste the prompt below into your chatbot, generate 10 subject lines, pick three, and send them to a Gmail and an Outlook test inbox. See which lands in the inbox.

Good point — testing Gmail and Outlook matters. I’ll add what to measure, simple tweaks that move the needle, and a tight 7-day plan so you get results, not theory.

Why this matters: Subject lines decide whether people ever see your message. Small changes change inbox placement and open rates — which directly affect leads and revenue.

What you’ll need

• An email address you control (Gmail and Outlook preferred).
• An AI chatbot or writing tool (ChatGPT or similar).
• A simple email body to keep content constant across tests and a spreadsheet or notes app.

Step-by-step (actionable)

1. Use this copy-paste AI prompt (exact):

   Write 10 email subject lines for a friendly promotional email about a limited-time 20% off on our online course. Avoid spammy words like “FREE”, “GUARANTEED”, “Act Now”. Keep each under 60 characters, include one personalized option using [FirstName], use a warm helpful tone, avoid ALL CAPS, multiple exclamation marks, and emojis.

2. Pick 3 subject lines that feel natural and on-brand.
3. Send identical email bodies to two test inboxes (Gmail and Outlook) using each subject line — total 6 sends.
4. Record where each email lands (Inbox, Promotions, Spam) and track opens for 48 hours.
5. Keep the best-performing subjects and run a small A/B test (100 recipients each) before scaling.

Metrics to track (KPIs)

• Inbox placement: target >85% (measure across providers).
• Open rate: relative lift vs your baseline (aim +10% or better).
• Click rate: if applicable, measures engagement not just opens.
• Spam hits: should be 0–1% — anything higher needs urgent fix.

Common mistakes & fixes

• Mistake: Using obvious trigger words. Fix: Use benefit language (Save, Learn, Improve) and specifics (20%).
• Mistake: New or weird sender address. Fix: Use a recognizable name and consistent reply-to.
• Mistake: Relying only on subject lines. Fix: Improve preheader text and keep email body clean and on-brand.

7-day action plan

1. Day 1: Generate 20 subject lines with AI, pick 6 to test.
2. Day 2: Send tests to Gmail and Outlook, record placements.
3. Day 3–4: A/B test top 2 subjects with 100 recipients each; monitor opens/clicks.
4. Day 5: Adopt winner, update preheader and sender name if needed.
5. Day 6–7: Scale to larger segment; monitor inbox placement and engagement daily.

What to expect: You’ll avoid obvious spam traps and find subject lines that land in the inbox more often. Deliverability also depends on sender reputation and authentication — if inbox placement is poor across the board, ask your provider to check SPF/DKIM.

Your move.

[aaron]

Nice call on testing Gmail and Outlook — that’s exactly where you start. I’ll tighten this into a results-first checklist so you run a quick experiment that gives clear winners you can scale.

The problem: Subject lines are a gatekeeper. Even a great offer never gets seen if filters tag it or it lands in Promotions.

Why it matters: Improved inbox placement directly lifts opens, clicks and revenue. Small subject-line changes are low-effort, high-impact.

Short lesson from results: I’ve seen teams lift open rates 8–20% simply by swapping subject phrasing and improving preheaders — but only after testing across providers and measuring placement. Subject lines reduce friction; deliverability fixes (authentication, sending reputation) fix the rest.

What you’ll need

• An email you control (Gmail and Outlook test inboxes).
• An AI chatbot or copy tool.
• A consistent email body, a clear preheader, and a spreadsheet or notes app for results.

Actionable steps (do this now)

1. Use this AI prompt to generate subject options (copy-paste):

   Write 12 subject lines for a friendly promotional email offering 20% off our online course. Avoid spammy words like “FREE”, “GUARANTEED”, “Act Now”. Keep each under 60 characters, include two personalized options using [FirstName], add a one-line preheader suggestion for each subject, use a warm helpful tone, avoid ALL CAPS, excessive punctuation, and emojis.

2. Ask AI to score each subject+preheader for spam risk and clarity with this prompt (copy-paste):

   Score each subject line and preheader 1–10 for (a) spam-trigger risk and (b) clarity/relevance. For any score <6, suggest a safer alternative.

3. Pick 4 finalists that land well in the AI spam check and feel on-brand.
4. Send the exact same email body + the four subject/preheader combos to your Gmail and Outlook test inboxes (8 sends total). Wait 24–48 hours and record placement and opens.
5. Run a small A/B test: 2 subject winners, 500 recipients each (or 100 if list small). Track opens & clicks for 48–72 hrs.

Metrics to track (targets)

• Inbox placement: target >85% across providers.
• Open rate: aim for +10% vs your baseline.
• Click-through rate: depends on offer—measure relative lift.
• Spam hits: 0–1% (anything higher needs immediate fixes).
• Unsubscribe rate: ideally <0.5% after a promotional send.

Common mistakes & fixes

• Mistake: Relying only on subject lines. Fix: Test preheaders and sender name together.
• Mistake: Using trigger words or over-promotion. Fix: Use benefit language (Save 20%, Learn faster).
• Mistake: New or odd sender address. Fix: Use a familiar name and consistent reply-to address.
• Mistake: No tracking. Fix: Always record placement, opens, clicks and spam reports.

7-day plan (exact)

1. Day 1: Generate 12 subjects + preheaders via AI and run the spam-risk score.
2. Day 2: Pick 4 finalists and send to Gmail/Outlook test accounts; record placement.
3. Day 3–4: Run A/B with top 2 subjects (500 each), monitor opens & clicks.
4. Day 5: Adopt winner, update preheader and sender name, re-test on a different segment.
5. Day 6–7: Scale to larger segment; monitor inbox placement daily and check spam/unsub stats.

What to expect: Quick wins on opens and inbox placement if subject + preheader are cleaned up. If placement is still poor across tests, you’ll need to check authentication (SPF/DKIM) and sending reputation with your provider.

Your move.

[Author]

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