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Practical Computer Advice
from Martin Kadansky

Volume 9 Issue 3
March 2015
I Attached My Files to an Email and Hit Send, but It Won't Go!

The problem
Has this ever happened to you? You want to share some files or photos with a friend or colleague, so you do the obvious thing:
  • You compose a new email message, or perhaps you chose Reply or Forward instead.
  • You fill in the "To" address, Subject, and Body of the message.
  • You attach the appropriate file(s).
  • You click Send.
And then, for some reason, this message just won't go. It seems to get "stuck" in your Outbox. (The exact location will depend on your particular email program, but for simplicity I'll use the term "Outbox.") What's going on? This has always worked before, what's wrong this time?

That stuck message might cause a bigger problem
When a given message has a problem being sent, some email programs will "time out" and move on to the next message you've queued up to be sent, and then eventually return to the problematic one to try again, so while that problem message may slow down the process, other messages can still go out.

However, other email programs may just keep trying to send that problem message over and over without moving on. In this case, that message has become a "cork in the bottle," preventing all other messages from being sent.

How to get your email program "unstuck"
If you've got a message in your Outbox that seems stuck, I suggest either moving that message to your Drafts folder or (if it's not very important) just deleting it.

However, if that problem message is currently in the process of being sent, some email programs (like Microsoft Outlook) won't let you do anything with it. In that case you'll need to "stop" or "cancel" the sending process first. Then you should be able to move or delete the message.

Potential explanations
There are a number of possible reasons for the inability to send a message, including:
  • The "To" address was entered incorrectly. Perhaps you entered the wrong address, or it's syntactically incorrect, i.e., not of the form "username@domain.tld" (where "tld" is "com" or "net" or "org" or "edu," etc.).
  • Your computer can't connect to your outgoing (SMTP) mail server. This has many causes, the simplest ones are that your internet connection isn't working, your mail server is busy, or your email account password has changed.
  • The size of that message (including all of the attachments) is so big that it just cannot be sent via email.
Email messages have a size limit?
This is one of those odd little computer secrets with big implications. For a number of reasons, including issues regarding security and storage, email servers limit the size of any single message. While there is no single maximum size that all servers use, in my experience you'll probably start to experience problems when the message you're trying to send is larger than about 8 to 10 megabytes (mb) in size. Some email systems like Gmail let you send messages up to 25 mb in size, but they only guarantee that that will work if your recipient is also on Gmail.

Why doesn't my email program notice this and warn me?
Your email software can't know in advance the maximum size to which any given email system limits its messages, and there is no protocol for email software to ask the destination server before sending a message. Wouldn't that be a great idea?

So what if you need to send something larger than that?
Well, here's where you need to get creative, and the solution will depend on a number of things, including how many files you want to send, how big they each are, and the people to whom you're sending them and what their needs (and computer skills) are. No single solution will fit every situation, so you may need to develop a variety of techniques.

Here's one expedient technique: If you're sending multiple files and each individual file is 8 mb or smaller, instead of attaching them to a single email (which probably won't work), break them up into groups totaling 8 mb or less, and then send each of those groups in separate emails. For a small number of files, this is a quick and simple solution, but for a large collection of files this is a lot of work.

Additional techniques that don't change what you're sending
The modern, sophisticated approach boils down to this: Don't send the files directly. Instead:
  • Upload them to a web site or server on the internet ("in the cloud"), and then
  • Send an email that does not have the file attached at all, but instead contains a link in the body of the message that will enable the other person to view the files online, or download them to their computer. This drastically reduces the size of the email you're sending.
The most common way to do this is to use a file-storage, file-sharing, or file-transfer company. Here are some popular services:
Note that many of these services offer free accounts with limited features, and paid (premium) accounts with expanded features. If security and encryption are important to you to protect the data you're sending from falling into the wrong hands, be sure to pick a service that includes those features.

Or, you could go "old school":
  • Depending on the number of megabytes you want to send you could burn your files to a CD or DVD or copy them to a flash drive of an appropriate size, and then send that via USPS or Fedex or UPS, etc.
Techniques that do change what you're sending
Consider these approaches, where you do some work on your end to change the data to a smaller size:
  • Make smaller or simpler versions of your files and send those instead. For photos, try reducing their resolution. For documents, try breaking them up into smaller documents, then sending those smaller documents in separate emails. For audio or video, consider reducing the quality.
  • Change what you're sending, if appropriate. For example, you could send only the essential information (a small sample, abstract, or teaser) instead of the entire thing. For audio files, you could make transcripts and send those instead of the recordings.
  • Find a way not to send the files at all. If appropriate, change the conversation away from the raw data. Send your perspective or analysis or conclusions.
Where to go from here
How to contact me:
email: martin@kadansky.com
phone: (617) 484-6657
web: http://www.kadansky.com

On a regular basis I write about real issues faced by typical computer users. To subscribe to this newsletter, please send an email to martin@kadansky.com and I'll add you to the list, or visit http://www.kadansky.com/newsletter

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Copyright (C) 2015 Kadansky Consulting, Inc. All rights reserved.

I love helping people learn how to use their computers better! Like a "computer driving instructor," I work 1-on-1 with small business owners and individuals to help them find a more productive and successful relationship with their computers and other high-tech gadgets.

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