Here are some things to try if your sent mail is getting stuck in the outbox (depending on our Outlook version, these may vary):

In Pre Office 2007:

1. In Outlook, click Tools > Options > Mail Setup.
2. Check “Send immediately when connected.”
3. Click on the Send/Receive button on the Mail Setup General tab.
4. Make sure both options to “Include this group in Send/Receive” are checked. Make sure that your account is included in the Group to send.

In Office 2007/2010:

1. Click The File-Tab (orange one) and choose Options in the left pane
2. Open the Advanced Menu (from the left pane)
3. Scroll down a bit in the right pane, and find “Send and Receive”
4. Make sure ”Send immediately when connected.” is checked.
5. Click OK
6. Click the Send/Receive Tab in the Ribbon
7. Click Send/Receive Groups
8. Choose “All Accounts Group (1)”.
   Alternatively you can customize which accounts to be sent automatically by choosing “Define Send/receive Groups”

Other Options

• Try registering the Outlook Send/Receive Library Manually: Click Start > Run and type regsvr32 inetcomm.dll
• Check to see whether an antivirus email check is slowing down the sending and receiving process. Try disabling AV and sending to decide whether this is the problem.
• Check to decide whether other programs running in the background are interfering. Disable them one at a time. This includes the firewall, anti-spyware, anti-spam, and all anti-malware programs.
• In the account settings, Advanced settings, change the server timeout time from 1 min to 5 min.
• Check to see whether outgoing mail server authentication is required. Try selecting that option in account settings and use same setting for the incoming server.
• If all else fails, create a new Outlook profile.

Setting up a second (third, fourth … ) account in Outlook.

Adding several accounts to your Outlook 2010 is a simple task. Using them and switching between them is also very easy. What you DO need to decide before adding several accounts is, which will function as your main account, and should the accounts use the same PST-file (the database storing your emails) or should you use separate PST-files ?

Functionality will be the same, no matter what you choose.

In the last section, I will give my thoughts on pros and cons using one or two PST-Files.

Adding more Accounts

1. Click the FILE tab (the yellow one)
2. Click the ACCOUNTS-button and then the Account-Link popping up underneath it.
3. Follow the steps found here.

Choose between the two

1. Start writing a new Email
2. In the top left corner you find the From, To, CC-buttons.
    

   Notice that the FROM-button now has a little arrow attached to it.
   Clicking it will allow you to choose which account to send from

If you have decided to use several PST-files, you may also choose which account to use by simply highlighting the appropriate InBox in the account/folder listing, before opening a new Email Document. Outlook will choose the account corresponding to the InBox selected.

Several Signatures

If you automatically want to add signatures to your new emails, you can set Outlook to use different Signatures for different accounts. Here’s how.

1. Start a new Message
2. Click the Insert Ribbon
   
3. Click the Signature Button
4. Choose Signatures from the drop down menu
5. In the Signatures Dialogue window,  Add and design a new signature

Connecting each signature to a different account

Setting this up, may not be very intuitive to you (Another Note to the Outlook developers). But it is rather simple one you know how.

In the right hand side of the Signatures Window there are three pull-down menus titled “Choose Default Signatures”. It would be fair to assume you choose these settings while creating your Signature, but that’s not it. They have no relations to the Signature creation what so ever. They really should have been put in a separate dialog window. But that’s another discussion.

After creating all of your signatures they will appear in the pull-down menus.

1. In the first pulldown menu, choose which email account to attach a signature to
2. In the second choose which signature to use (if any) when starting a new Email
3. In the third one, choose which signature to use (if any) when replying to an email

The settings are stored immediately and you do not need to close the Signature Window until you’re all done.

Using One or Two PST-files ?

The following reflects my experience. You may experience it differently, and if so please feel free to add your own comments on the matter.

Choosing one PST-file may slow down performance when the one file get large. On the upside, you will only have one set of folders to worry about (one inbox, sent box, deleted items etc.). You will also not need a large monitor to see all inboxes at once in the folder/account listing.

Choosing two PST-files may increase your security and performance as the files will be smaller. Backup and deleting an account will be easier. You get more control over each account. On the downside, you will need a large monitor to be able to see each inbox in the folder/account listing, and you are not able to choose which folders to display in the listing except from expanding (or collapsing) the entire account folder (NOTE to the developers; add this functionality in the next Office)