Overview
Links are useful, but sending them at the wrong time is one of the easiest ways to hurt your deliverability. Carriers and Apple treat unsolicited links as a strong spam signal, and recipients do too. Follow these guidelines to share links safely.Don’t send links before a reply
This is the most important rule. If someone hasn’t responded to you yet, do not send a link. Messages with links sent before a recipient replies are significantly more likely to be flagged as spam. Only share links after the recipient has responded and shown interest.How link previews work
Links behave differently depending on whether the recipient has replied:- Before a reply — links appear as plain text (no preview embed) and carry higher spam risk
- After a reply — links display with a rich preview (title, image, description)
- Once the recipient replies, any previously sent links also become embedded retroactively
Start the conversation first
Don’t lead with a link. Open with a question or relevant message, wait for a response, then share the link when it’s naturally part of the conversation.- ✅ “Hey, are you still looking at properties in Charlotte County?” (They reply yes.) “Here’s the one I had in mind — [link]”
- ❌ “Hey, check out this listing! [link]“
Give links context
A link dropped into a conversation with no explanation feels like spam. Introduce it naturally so the recipient understands what they’re clicking and why.- ✅ “I put together a quick walkthrough of the lot. Take a look when you get a chance — [link]”
- ❌ “[link]”