You can’t just give your emails a packed lunch, a kiss on the cheek, and send them into the wilds of the Internet expecting them to make it to their destination safely. It’s a dog-eat-dog world out there, and emails need to be pretty streetwise to navigate the many obstacles between them and a reader’s inbox.

In Hotmail, for example, your message will have to endure interrogation from up to four different filters. Such measures are taken to protect inboxes from junk, but legitimate business communications are often wrongly labeled as spam and blocked from being delivered.

The problem is even worse if corporate gateways have been deployed. Consumer ISPs cooperate with each other to fight spam and usually provide a mechanism for users to review spam and report any that were mistakenly spiked. Corporate gateways, however, don’t have this safety valve, so your messages can end up being deleted before anyone sees them or has the opportunity to mark them as non-spam.

So how do you grant your emails safe passage through the web’s many gateways? It’s never a guarantee, but there are some steps you can take to improve their chances when faced with the prying filters of email clients.

1. Send something of value

Yahoo says that if messages are wrongly classified as spam, users are quick to alert them. If you’re sending useful, entertaining or valuable messages, your recipients will lobby their email provider to make sure your messages get through.

2. Avoid spam-like messages

Today’s anti-spam systems include a vast number of parameters to estimate whether an email might be spam or not, and tot up a probability based on that. It can be challenging to work around all the parameters, but there are some basics to always follow, such as balancing the ratio of images to text and avoiding spam-favorite keywords like “free.”

3. Test everything

Run your email through a border gateway product like MIMEsweeper to see what traits of your message might be misconstrued as indicating spam. Get a clean assessment from your test gateway before trying to send your message through real gateways.

4. Monitor bounces

Look for trends in bounces to see if a particular ISP or company is blocking your email.

5. Manage removals

Spam is in the eye of the beholder. If someone no longer needs your messages, honour their removal request promptly. If you don’t, they’ll add you to their spam filters and you risk the ISP blocking all your future messages. Take off persistent bounces too – some ISPs will consider you a spammer if you send email to too many invalid addresses.

6. Form alliances

Contact ISPs and companies who are blocking your email and ask to be whitelisted. Remember, their customers have asked to receive your communications and they have no right to stop them getting through. Many ISPs publish tips on getting messages delivered to their customers and procedures for accrediting bulk emailers. See, for example, AOL’s and Hotmail’s postmaster pages and Yahoo’s mail FAQ. The challenge of deliverability is another reason why more and more companies are working with email marketing specialists like StoneShot. We have established relationships with major ISPs and are known as a reputable bulk emailer.

If you’d like to talk about how StoneShot’s technology and consultancy services can make your campaign more effective, email us at