Hi all,

I experienced the problem described below for quite some time already.
Recently, I had the "opportunity" to re-install my PC :-(
The problem didn't disappear, so let me submit it.

Short problem description:
My Outlook contains a POP3 as well as a Exchange account.
In case I'm not connected to the Exchange account, I can't send any mail from my POP3 account through SMTP to a mail address that was not used before.
Message: "Outlook must be online or connected to complete the action"

I tried in some more detail to log my installation and to reproduce the issue.
Here my conclusions...
Software versions:

• Windows 7 x64 SP1
• Office 2010 Pro SP1

Step 1:
Configure a normal POP3 connection to a POP3 server on the internet. Sending through SMTP. All default settings.
This works fine, as expected.
Import an existing PST file (containing contacts, mails, agenda items from a previous installation).
Step 2:
Add an Exchange connection to an Exchange 2007 server. All default settings.

• This gives the expected warning that Exchange now takes its own delivery location. Just press Ok on this warning.
• Still in the account creation dialog, I select the POP3 account to be the default account (iso the newly created Exchange account).
• Then I start Outlook. Effectively, the delivery location is on the Exchange, showing the Exchange calender etc in the home page. Since I don't want that, I immediately change the delivery location to the POP3's PST file (through File | Account Settings | Data stores)
• Then I restart Outlook
• Everything seems fine: send/receive mails through POP3 and/or Exchange, just as expected

Step 3:

• Make sure you cannot connect to the Exchange server anymore (e.g. by going home, leaving the office network... that's what I did).
  Outlook now shows a yellow triangle, indicating that there is no connection to Exchange. Fine.
• Click on the Inbox of the POP3 account and create a new mail.
  
  
  Send a mail to a well-known mail address (I mean, one to which you have sent before)
  This works fine.
• Do the same, but now to an address that you've never used before.
  Outlook shows a message (pop-up from the system tray: "The connection with Microsoft Exchange is not available. Outlook must be online or there must be a connection to finish this action.".
• It then refuses to send that mail. Other mails can still be sent.

I have the feeling it tries to add the "newly discovered" email address to the Exchange's contact list and fails to do so (disconnected) and as a consequence refuses to send the mail.

Any help would be appreciated,
Johan

After reviewing your configuration / steps, did you re-establish an internet connection to another LAN or WAN?

If you are not connected to the internet, your mail server is not receiveing your request.

Hi SpiderTech,


I typically have two accounts active at the same time:

• POP3/SMTP private
• Exchange professional

Both are configured as described in my Outlook 2010.

When I'm at home, I'm disconnected from my office network.
My normal internet connection is ok, so I'm still able to send/receive mails using POP3. No issue with that.

Only, as stated above, when I try to send a mail through my POP3/SMTP account to a contact to which I didn't send a mail before, Outlook refuses to send the mail. It then seemingly requires a connection to the Exchange server.

That's my real problem: why does Outlook "require" that Exchange connection if I only want to send a mail through SMTP? I have the feeling it tries to update an Exchange based "recently used addresses". I can't find any proof of that and I don't know how to disable it if that would be the cause.

Regards,
Johan

This SMTP address being used, that is receiving the disconnection status, is this an email alias of the excahnge server primary email address?

The reason i am asking this, if you are using any address associated with your exchange account, than you will need to authenticate to that SMTP server to send email.

I also have an exchange service and several POP accounts, not associated with my exchange service, and 2 POP SMTP only alias accounts. These alias are associated to my exchange account and require me to be connected to authenticate before any email is sent out using the SMTP servers.

Keep me posted.

Sorry for the delay in my reply. This forum doesn't seem to warn me about posts, although I requested so...

The POP account is not related to the Exchange one in any way.
The Exchange is my professional one, POP is an independent private one without any SMTP authentication required.

Oh, and maybe this may also be helpful...

My configuration is as follows (taken from File | Accounts):
* Email:
- Johan@mycompany POP/SMTP (standard, send/receive from this account)
- johan@myother Microsoft Exchange
* storage files
- Internet calendars c:\users\Johan\Appdata...\InternetCalendar-Johan.pst
- johan@myother c:\users\Johan\Appdata...\johan@myother - Johan.ost
- johan@mycompany c:\local\mail\johan@mycompany.pst
* Addressbooks
- Addressbook for mobile devices MAPI
- Outlook-adresbook MAPI
When I open "Contacts", the navigation panel on the left hand side shows:
- Proposed contacts - johan@mycompany
- Contactpersonen (these seem to be tied to Outlook, because they are named "Contactpersonen" Dutch for "Contacts", which matches my Outlook language)
- Contacts (the English named set of contacts, which matches the language of my Exchange. They got added when I added the Exchange account)
- Proposed contacts - johan@myother

All of the information you have provided seems to be in order.

In all attempts to reproduce your scenario have come up with no answers on my end.

This is what i have done:

Using a laptop, Configured an Exchange account profile to my work exchange account.

Within the same profile, connected 2 POP accounts and 2 POP SMTP accounts. The SMTP are for me to use email alias i have configured.

Attempted to Disconnected the Exchange account. This could not be done without removing internet connectivity. So i selected "Work Offline".

This disabled the Exchange Account and the POP accounts as well.

See if you can toggle the work offline feature to see if your Outlook reverted to an Offline state after you leave your office.

Keep me posted,

I do not fully get it...

You suggest to toglle "Work off-line", but then my POP/SMTP will not work for sure (just like you mentioned).

In my case the Exchange server is not reachable in case I leave the office. I can perfectly be connected to "the Internet" without having access to exchange. I suppose that your Exchange server is publically available, correct?

I've followed the following strategy:
* Put Outlook off-line (PC remains connected to internet)
* Try to send a mail from the POP account
* Send it
* The mail now remains in my outbox, which is to be expected.
No message is shown at this moment, it is just put in outbox.
* Explicitely click on "Send & Receive". The mail now gets sent without problems.
* Toggle on-line
* Create a mail to another new address, still using the same POP account.
* Send it
* Now immediately the message comes that outlook needs to be connected in order to send.

:-(

It appears we have tried everything, relative to troubleshooting this issue. It would seem the disconnection to your Exchange Account is causing the other accounts in that profile to fail. All testing proves this.

The only viable solution is to remove the POP accounts from the Exchange Profile and create another specifically for the POP accounts. You can than toggle the profiles.

will keep searching for another solution rather than a work-around.

Best regards.

Hi SpiderTech,

That is exactly what I'm using for the time being:
* One profile with both accounts
* One profile with the POP account only

That works fine.

Since the problem reoccurs after a clean installation, I guess it is a consistent issue. Additionally, such a scenario doesn't seem very uncommon. That's why I'm quite surprised not to find anyone (well, Google doesn't find any ) experiencing the same issue.

I'd like to thank you for your time analysing the issue and for your suggestions.

Greetz,
Johan

I was "Googling" for something else and came across this forum/thread, and I just had to comment, so I had to join the forum :-)

I'm running Office2010 with ONE, SINGLE PROFILE configured with two Exchange accounts (one work, one 1and1.com) as well as a POP3/SMTP account just fine.

Were you able to go back to your original setup and have both as well?

Hi BWB8771,
Nope, I didn't have any success going back to my desired environment.

I can perfectly use both as long as Exchange is available.
Once Exchange is not reachable, my POP3 fails to send to some addresses.
As far as I can determine it consistently fails on those addresses that I didn't use before...

If you would happen to have any suggestions, I'd be glad to try.

Thanks,
Johan

Yes if Exchange is unavailable then the exchange account will nee to be configured so it is working or Outlook will not process correctly.

Since Outlook always sets Exchange accounts as default, when they no longer function Outlook will have trouble sending/receiving as long as it is active.

Note: Setting another account as default did not work for me.

I fixed the problem by going to Address Book, clicking on Tools/Options and chaning the setting in Addressing from "Start with contact folder" to "Custom".

Hi leondigiduck,
I immediately tried your suggestion but for me it doesn't seem to change anything.
Did you choose a specific order for the items in the "custom" list? I tried several, but when not connected to Outlook and trying an addres-never-tried-before, it still says that it must be connected to Exchange in order to be able to send the message.

Maybe you did it slightly different than I did anyway.
Could you provide more details?

Johan