5 Easy Ways To Ensure Your Email Is Sent Properly

By and large, email hasn’t really changed all that much. The way it’s sent and received is more or less the same way it’s always been.

What has changed are the methods mail providers employ to stop spam, and email size limitations.

Here are the 5 things you can do to ensure your email is sent properly.

1. Use plain text

Plain text means unformatted, and that means text that has no styling to it. No bold, italic, underline, colors, etc. Just plain raw text.

HTML formatted text is usually labeled as “Rich Text”. Popular email providers like Hotmail and Yahoo! Mail do have a small drop-down menu where you can easily switch from Rich to Plain. Windows Live Mail can switch to plain text by tapping ALT on your keyboard to show the menu bar, then click Format then Plain text at the top. Mozilla Thunderbird by default will ask you on send of any email whether you want to send in HTML, plain, or both.

You do not have to exclusively use plain text, but for really important email replies that you want to give every chance of being received properly by the recipient, use plain text.

2. DOC or PDF?

It is common that people attach documents to email, however the preferred file type that email systems “like” are PDF files. This is due to the fact that it is far less likely to contain any malicious code in it compared to a DOC.

When sending attached documents in email to people, send a PDF instead of a DOC. You can easily create PDFs using the freely available PDF Creator. This will create a virtual printer so you can click File/Print and “print” your document to PDF. It can be done with any program that has the ability to print.

3. ZIP files and knowing how big is too big

Generally speaking it is OK to attach a ZIP to an email. For a while it was expressly forbidden as just about all email providers would not allow them, but today that’s not the case.

With ZIP files, the thing to bear in mind is to send them only when you have to. People used ZIP originally because it compresses files into smaller ones that were suitable for people who didn’t have a lot of space in their email accounts. Being that everybody has gigs of space, you no longer have to worry about that.

When should you use a ZIP?

If sending to a personal email address and the total size of your attachments goes over 5MB, use ZIP. While it’s true that mail systems like Gmail, Yahoo! Mail and Hotmail all allow 10MB (and in some cases 20MB) emails, the general rule of thumb is to stay under 5MB.

If sending to a work/corporate email address, the unofficial limit is 2MB. This is because there are many corporate environments that have positively ancient email systems that won’t allow incoming mail to be over that size.

Quick tutorial on how to use 7-Zip to break up a large single file:

7-Zip is a freely available archive program that supports ZIP, and has the very easy ability to break up large files into smaller ones suitable for attaching to email.

Let’s say I wanted to send PDF Creator to somebody in email. Here’s the file:

This file is 17MB in size. It’s far too large to send in email, and in most email systems it won’t even allow me even to attach it because of how big it is.

We’ll say that I want to send this to a corporate email address which I know won’t allow more than 2MB emails at a time. I can use 7-Zip to break this up into 2MB ZIP files that the recipient will be able to receive.

First I right-click the file, choose 7-Zip and then Add to archive…, like this:

In 7-Zip, I change the archive format to Zip, like this:

In the same window under Split to volumes, bytes, I type in 2M (for 2MB), like this:

..and then I click OK in 7-Zip.

This created 9 ZIP files, none of which exceed 2MB, like this:

This will require me to send 9 emails to get this out to the recipient, but the point is that it will work.

The recipient on download of all 9 emails can save the attachments to a directory, open the first 001 file with 7-Zip or WinZIP and the entire archive will open up, allowing the recipient to use the original 17MB file.

4. Avoiding certain words and phrases

It’s not the curse words you have to avoid but rather the common ones that spammers use.

For example, many people have “viagra” set up as a filter in their email to deter spam. If you use that word in your subject line or body of the email you send, chances are very high it will be flagged by the receiving system.

Other no-no words and phrases are “cialis”, “university diploma”, “overnight success” and basically all the other common things spammers typically use.

If you simply don’t use what they use, your mail will go through.

If you’re in the situation where you have to use words and phrases like that, remember tip #1 above, use plain text. That should be enough to allow your mail through (but if not, you’ll know why.)

5. Use the outgoing server that belongs to the email provider

(If you use webmail, you don’t have to follow this step.)

The choice of the outgoing, known as the SMTP (Simple Mail Transfer Protocol) server, used by your mail client is important, because some mail servers don’t “like” it when you use one that doesn’t “match” with the email address you’re sending from.

Using Gmail as an example:

Gmail has the ability to download via IMAP or POP, so you opt to use a mail client to get your mail that way. But then you discover that Gmail’s outgoing mail server is a bit too slow for your liking, so you use your ISP’s outgoing server instead which is much faster.

The potential problem that can happen with this is that you’re sending from an @gmail.com email address but the outgoing server header in your email doesn’t have gmail.com anywhere in it. Some overzealous mail servers will flag that as spam because it believes it to be a spoof. This doesn’t happen often, but there are instances where it still occurs even today.

You can avoid your mail being falsely flagged by using Gmail’s outgoing server with a Gmail account in your mail client. Yes, it will be slower, but those few extra seconds you have to wait are worth it knowing there’s basically no way a receiving mail server will “see” it as a spoof.