The ‘Oh shit!’ email rule

I don't normally do these kinds of posts on this blog, since I like to keep it very technology focused on factories, but I just had to share this - hoping it could help yourself avoid some of the stoopid mistakes like the ones I've made over the last few years.

Every now and again I make a real embarassing blunder in my email correspondence. It's happened a few times in the past, and I can see at least three scenarios that pop up every few months or so, and its at times like these you just want to bury your head in the sand, as your credibility tumbles.

  1. You automatically 'ReplyAll' instead of 'Reply' and copy your rather personal response, (intended only for the sender of the message), to everyone and sunder - making you look like an idiot.
  2. You reply to a mail with a beautifully crafted response, one that has taken a few hours to compose just right, and about 20 sec's after you send it, you realise you forgot to provide the one piece information the thread required from you. Sometimes this is the just the attachment to the mail.
  3. Whilst writing a mail, you forget someone's name or email address, someone who is either in your organisation or someone you received mail from in the past, so you quickly type it in the CC line, and expect it to resolve. Once you obtain the right contact name or email, you continue writing the email, and totally forget to remove it from the CC. More often than not, that's the last person you want the email to go to, since they are probably the subject of your response to the people on the To line.

The irony about cases 1 & 3 is that your error burns in the back of your retina as you release the mouse button over the 'Send' button - and just as the explicative's form in your mouth, and the sweat starts - "I didn't really do that, did I!?!".

Because your email client (mine is Outlook) is so optimized for sending email responses so quickly, you scramble around to try and find that 'Recall This Message...' command, which is never where you expected it.

[In case you are wondering where it is nowadays in Outlook 2007, you need to open the sent email, (hopefully it is in your sent items folder), then the command is on the 'Other Actions' menu - good luck, sods law is against you here.]

Anyhow, you are likely very doomed by this point - as your mail wings its way across the interweb. Most people nowadays are very quick to pick up their email (thanks to mobile devices), and all you can hope for is that the someone you didn't want the email to go to is either asleep or offline - yeah right! - both cases pretty unlikely in your present predicament.

A Solution

An obvious solution to these problems is to delay the email from being sent, giving you that little bit of time to correct the err's in your ways. In Outlook, you have always been able to do this by setting the 'Do not deliver before' time in the Options of the mail.

The problem is that you have to do this for every email (per instance), and if you are in a rush for example - which we are most of the time, you may forget to do this for every mail. (It's a shame Outlook doesn't have this as a global setting).

For ages I have been meaning to create an add-in for Outlook that gave me 2 buttons on my mail, the first one (the big default 'Send' button) called 'Send' automatically delays the email for a configurable amount of time (say 10 min's), and a smaller button called 'Send Immediately' sends the email immediately (without the delay). You would also have an options dialog somewhere to configure the delay amount, and some other minor options that escape me for now.

However, I have not had the time to create this add-in and recently I was struck by this issue again - much to my demise.

A Better Solution

I was speaking to a mate of mine at work about this last incident, and sharing the embarrassment, when he suggested you can set up a rule on your outgoing email to achieve the same thing.

I didn't really believe him at first, because if this were true, surely I would have heard about it before. This is surely a known user issue, and everyone who uses email (everyone then!) must have experienced this before, surely it would be out-of-the-box functionality and we would all know about it!

Anyhow I decided to check it out and to my amazement its real easy to setup. Here goes:

  • In Outlook, goto Tools | Rules and Alerts.
  • Click 'New Rule' to run the Rules Wizard
  • From the list of rule templates, select the one that says 'Check messages after sending'
  • Put in your filters for what types of messages you are after - if any. I didn't define anything here so this means apply this rule to all messages I send.
  • Then in the select actions list, select the last one in the list called 'defer delivery by a number of minutes'. Then define your minutes - say 5 or 10.
  • Complete the wizard.

OK, and to test, send yourself an email message, and it should sit in your Outbox for the number of minutes you defined. To check this, open the email, and look at the email options, you should see that the rule has set the 'Do not deliver before' time to whatever in the future.

In Retrospect

So, this solution is easy, anyone can do it and it doesn't require installing anything to each machine you run Outlook (for example at home and at work). The rules get updated for all instances of Outlook.

I have not tested this on OWA (Outlook Web Access), but I suspect these types of rules don't work in OWA.

The only issue I see, is that I don't have that 'Send Immediately' command I wanted for my add-in. In these cases, I will need to go into my Outbox and clear the 'Do not deliver before' flag on the mail per instance - bummer, but its probably a good thing in the big picture.

Comments (10)
  1. Simon says:

    If you had that button I guarentee you’d just get used to pressing it and do the same thing all over again. 😉

  2. Martin Brewer says:

    You can have another condition in your rule that looks at the body of your email for a phrase (like ‘SendNow’) if this phrase exsists the rule is not invoked.

  3. Jezz Santos says:

    Thanks Martin,

    I was also thinking that the rule could be applied to filter email with an arbitrary custom property.

    We could then customize the default email form, and add this custom property (say boolean), and have a button on the form to set/reset it.

    Now when the rule fires, it can check this custom property and delay the send or not.

    This would get around the behaviour that Simon illustrates too!


  4. tony roth says:

    I just wish there was a rule that would prevent me from being an idiot!


  5. Jezz Santos says:

    Hi Tony,

    If and when you find that rule, you’ll be sure to share it eh?


  6. LockSmithDon says:

    I’ve had this rule in place for about a year now. What a godsend! It has saved my ass a number of times and I only have it set to one minute.

    This might be helpful … the one minute I use doesn’t necessarily mean a whole minute. As soon as the second hand passes the 12, you can hit "Send/Receive" and the message will immediately leave your outbox. I do this if someone is waiting on it.

  7. Dude this is totally awesome. I wish I had knew about this before. I can’t tell you how many times I rush to go offline immediately after I press the ‘Send’ button in order to prevent that message that i either a. replied all on and should not of, or b. had a serious type. I am adding this rule immediately!

    BTW, Another outlook add-in idea I keep thinking of is a ‘do not bug me’ on my inbox. Basically once you set it email pours into your inbox, but you don’t know it’s there. Then you can press some kind of ‘preview’ button to show you how many messages you have. You can accomplish some of this functionaliy buy working offline, but as soon as you go online all you messages stream in. This functionality would allow you stay online, write email messages, etc but not get distracted by incoming mail.

  8. Jezz Santos says:

    Thanks Don,

    I am user-testing the best delay for me, I think I will need more than <1 min though. (takes my brain longer to register my deficiences).

    I started at 10min, but often I have to wait for immediate responses to leave. I’m going down to 5mins now.

    I also noticed, that you can’t seem to change it once set. This must be a bug I reckon.

    Once you send the message and it sits in your outbox, try re-opening it and changing the delay (or even remove it). Then don’t forget to re-send (otherwise mail becomes a draft sitting in outbox forever).

    However, changing the delay does not affect the mail, and it still waits for the originally designated time. Your changes are actually ignored! – Check it out yourself!

    I need to reconsider the original proposal for an Add-In, and have that ‘Send Immediately’ button!


  9. Jezz Santos says:

    Hey Glen,

    Nice one.

    For your other idea, if you don’t want to go the whole hog with an Add-In (which I am also tentative in doing) you could infact create a macro and a temp folder to do what you want (I think).

    How about, creating a rule that moves all incoming mail to another folder call it ‘JustArrived’). Then create a macro and toolbar button to invoke it to copy all mail from JustArrived’ to Inbox?

    Dunno, if that might fix it for you.


  10. N says:

    Perhaps the best solution is to give the rule an exception, excluding those items with a certain category, e.g. "Send Immediately". I think that might be cleaner than looking for text in the body or subject.

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