Why won't Outlook cooperate with me when I want to schedule an email to be sent at a later date/time?

With some trepidation, I have to ask: is your computer on or off at the time that the sending is supposed to take place? and if on, is Outlook active? Also, how are your general Send options set up? When I was an Outlook user, I had the program set to send only on Send and Receive clicks and never automatically so I had time for second thoughts.

Forgive me if this is a stupid question. It’s not meant to be insulting, just information-seeking.

I’m not insulted at all, haha. I have no clue what I’m doing!

The computer is always on. I haven’t been on the remote server at the times they are to be sent (sleeping!), however, it says my “programs will keep running” when I sign off the server. I’m assuming that means Outlook is still running, but I’m not really sure about that. Originally, I did a test run (sent a scheduled email to myself) and signed out of the server, and I got the email right on time. I don’t know why it would send some but not most others.

I’m a complete newcomer to Outlook, so I’m not at all sure what my settings are. I’ll have to poke around.

Also, is your computer clock set to your real local time? and is Outlook’s clock set to the same time?

It’s hard to tell, a couple of questions as well below,

1) It sounds like you’re running remote desktop to get the server, is that right? When you go to leave, are you going to “log off” or just closing the session window on your side?

Logging off will stop all programs you have open. Just closing the session will leave you logged in and everything running as you have left it. The easiest way to tell for sure is if you go to log in next time, and all your programs are still up and running, then you’ve just closed the session. It also lets you know nothing else is logging you off.

Depending on the configuration and purpose of the server, even if you’re just closing the session, they may either power it down every so often, log all active accounts off to run backups, or even have a maximum time for security purposes.

2) Do you know if they use an Exchange server? It should let you know under the Tools -> Account Settings (menus vary), if it’s Exchange, then it may accept your message to delivery later even if you’re not logged in.

If it’s POP3 or IMAP it won’t and unless you’re still seeing outlook running (and the mail in your outbox) when you first log into the server again, this isn’t going to work.

Can you get the mail on your own computer somehow instead? If people get the mail anywhere off the internal network, then the answer is probably yes. It would really simplify things and give you more control.

3) What version of outlook? There are two ways to delay messages on the one I have in front of me (2007) and a quick look online shows their basically the same on different versions, but there are a few quirks.

Neither is really meant for what you’re trying to do. One delays messages until the first “Send/Receive” after a date and time, and the other delays messages a certain number of minutes in case you want an “ohhh shit” period to correct mistakes.

It looks like there are some third party plugins that might help.

SendLater looks promising, and has a free version. I haven’t used it, but says it doesn’t need to be running to send. Not sure if that’s accurate or marketing, but worth a shot.

This is getting long, so I’ll leave it at that. For what it’s worth, I have the same problem, and ended up directing everything through gmail (you can send from other accounts) and then using Boomerang for Gmail to deliver messages without freaking people out that I’m up at 4am.

Now if I could just get them to quit calling my cell to follow up right at 8:02am because they “just got my email”... ;)

Just wondering, anyway: why not go ahead and send when you’re ready to send? What difference does it make if the recipient gets something you wrote in the middle of the night? It’ll just be there waiting when the person logs in.

I once had a coworker who kept odd hours. It was not unusual to receive a message from him that he’d sent at 3 a.m. The timing didn’t take anything away from the content.

Lately I’ve been getting messages from a friend who appears to be writing in the middle of the night. I knew something was odd when I started receiving messages with time stamps six or seven hours into the future. (She lives in my time zone.) Turned out her system clock had been reset somehow to UTC and she hadn’t bothered to change it.

@Jeruba – it depends on the audience, but when I’m sending email for a client I don’t know well, I’d rather it didn’t have a 3am timestamp. There are a couple of reasons

1) It’s pretty easy to assume I’m working at home, I don’t always want to set that precedent
2) I’d rather limit our relationship to business hours, if I’m always up late, they can call at 11pm, right?
3) People have a negative connotation for late night, some assume you must be up “because” of something. Am I sick? Did the baby wake me up? Just get home from drinking? As a small business I do what I can to appear professional, that includes hiding my unprofessional hours. If you disagree, imagine your lawyer consistently sent you emails at 3 in the morning. Would you eventually wonder?
4) I’m not responsive in the mornings unless I have something scheduled, people who are morning people tend to think if you’re sleeping after 9 it’s because you’re lazy or lack self discipline. Maybe that’s it, but if so I’ve lacked self discipline for close to 20 years now and it’s not a problem when the alarm goes off, just when the eyes won’t close.
5) People have a tendency to suggest I quit working so late and that would of course fix my sleep problems so I didn’t have to “sleep all day”... thanks

So I tend to send emails in three bursts, lunch, end of business, and late night scheduled for early morning.

@augustlan I am no expert, but I would think you need to be on the server for emails to go out. When you go back to your email after being off for hours and open outlook are the new unread emails already there? Or, do they have to download? If they need to download then I would assume you are not sending and receiving in the state that you now leave your computer when you are away from it.

if you can’t get it to work, maybe just put them in drafts until 5:00am and then send them all out, before you go to bed. That isn’t really the middle of the night.

@funkdaddy Yup. All those things. Most of society looks down on nocturnal people.

Excellent advice for all us client-serving jellies, @Jeruba. Thanks very much.

@augustlan If you don’t want people calling your cell at 8:02 AM, try having your e-mails land in their mailbox when you DO want to talk to them. Or turn off your phone so all messages will go to voice mail, and sleep soundly.

I looked into it further, and it seems that even though I leave Outlook open (and tried leaving my remote server session up and running the last time), the server kicks everything/one out after two hours of inactivity. There doesn’t seem to be a decent work-around for that situation. What I’m doing now is sending the emails to my boss (in the middle of the night), with a list of intended recipients. She then sends them out in the AM. It works, but it’s clunky. Extra steps for all of us.

If these were just emails to coworkers, I’d send them in the middle of the night with no worries (they all know I’m working those hours). But these emails are going out on behalf of the organization I’m working for, to their members/clients. The organization prefers not to have crazy times on their business emails, understandably.