3 Workarounds For Overzealous Email Spam Filters When Sending Mail

Chances are at some point you’ve had your email flagged as spam by mistake by the people you send mail to regularly; it doesn’t happen all the time, but enough to annoy you.

Starting in 2010 and carrying on into 2011, for whatever reason all the major webmail providers started employing spam-prevention method patterns that for many are proving to be much too strict. Fortunately there are some workarounds for this.

1. Text-only email signature

Some mail providers really, really don’t "like" it when you have an image in your signature; changing it to text-only in many instances will cure the ill of having your sent mails false-flagged as spam.

2. Purposely setting a reply-to address

All email both for webmail and client has the ability to set a reply-to address, and ordinarily this is something you never have to bother with – but – if you’re encountering false-flagged spams on mail you’re sending out, enabling this helps deter those false-flags.

Enabling a reply-to is easy and you only have to do it once. The only thing you have to do here is set your reply-to address exactly the same as your existing email address, save the setting, and that’s it.

Yes, this is redundant, but it genuinely does help deter false-flagged spam for mail you send out.

- – Setting a reply-to in Hotmail – -

Go to Hotmail Options > Reply-to Address

Select Other address and purposely set to be exactly the same as your existing Hotmail address, then click Save.

- – Setting a reply-to in Yahoo! Mail – -

Yahoo! Mail Classic: Top right of screen, Options > Mail Options

Yahoo! Mail "All New" version: Top right of screen: Options > More Options

Yahoo! Mail Beta, Top LEFT of screen: Options > Mail Options

Accounts > Yahoo! Mail

Change reply-to address (text link)

Enter your reply-to the same as your primary:

Save Changes button:

- – Setting a reply-to in Gmail – -

Gear icon (top right of screen) > Mail Settings:

Next to "Send mail as", click edit info at the far right:

A pop-up window will then appear. Click "Specify a different reply-to address" and set to be your existing Gmail address, then Save.

3. Don’t quote the message on reply

This one is a bit of an odd duck but does work.

There are times when it’s the quoted reply of the person you’re replying to that triggers a false spam flag on send. Strange but true in some instances.

The solution to this is easy – don’t include the quoted text. You can simply highlight and delete it from the message before sending. It’s probably true that mail which is false-flagged as spam on send only happens for specific recipients, so you don’t have to turn off quoted replies completely.

Is it possible to disable quoted text completely?

This is a feature reserved mainly for mail clients and not webmail.

Hotmail and Gmail DO NOT have the ability to disable quoted text, so you’ll have to do it manually.

Yahoo! Mail is one of the very few webmail providers that allows for complete disabling of quoted text in a reply; it’s the very last option from Options > General and is a check box:

I don’t recommend disabling this however because it can prove to be an annoyance very quickly. You’re better off manually removing quoted reply text for those addresses that false-flag you as spam by mistake.