Howto use mail.tokkee.org with Microsoft Outlook (Express)

Version: 0.1 (2006-02-27): Initial release
Version: 0.1.1 (2006-03-05): Fixed a typo ;-)

Content

What are those SMTP, IMAP, POP3, ... thingies? (disambiguation)
Introduction to mail.tokkee.org

IMAP vs. POP3

Setting up Microsoft Outlook to use POP3

Step 1
Step 2
Step 3
Step 4
Step 5
Step 6
Step 7
Step 8

Setting up Microsoft Outlook to use IMAP

Steps 1-6
Step 7
Step 8
Step 9

Problems
Sending e-mail

This howto is intended for users of the mail.tokkee.org e-mail services. It describes howto setup the Microsoft Outlook/Outlook Express e-mail clients. Originally, the only way to send e-mails using my e-mail server was by means of "Autheticated SMTP". However, I did not get Outlook to work with this setup so I simply decided to add support for pop-before-smtp and imap-before-smtp. Well, some of you might ask, what all this means. Let's first explain some basic terms used throughout this writing.

What are those SMTP, IMAP, POP3, ... thingies?

SMTP: SMTP (Simple Mail Transfer Protocol) is a protocol to exchange e-mail messages between different computers on a network. For example it is used to send an e-mail from a client (a.k.a. MUA, e.g. Outlook) to an e-mail server (a.k.a. MTA, e.g. the e-mail server running on mail.tokkee.org). It is formally defined in RFC 821 and (in a revised form) in RFC 2821. For more information see this arcticle at wikipedia.org (german version).
ASMTP (Authenticated SMTP, a.k.a. SMTP-AUTH): This is an extension to SMTP that adds a way to authenticate and effectively log into the e-mail server. This is a way to prevent that anyone is able to send e-mail using any e-mail server. Only users who provide a correct username and password combination are allowed to send mail. ASMTP is defined in RFC 2554. More information is available at wikipedia.org (german).
IMAP: The "Internet Message Access Protocol" allows a user to access and manage e-mail on a distant e-mail server. An important point is that messages are kept on the server and are only accessible while the client is online. This provides faster access times with the drawback that you have to be online all the time while reading your e-mail. IMAP is defined in RFC 3501. Again, more information is available at wikipedia.org (german).
POP3: POP3 (Post Office Protocol version 3) is another protocol to access e-mail on a distant server. In contrast to IMAP, however, you only need to connect for a short time to download all new messages. After that the messages are locally stored on your computer. It is defined in RFC 1939. (wikipedia.org | german).
pop-before-smtp / imap-before-smtp: This is another way to allow only specific users to send e-mail. A user "authenticates" by retrieving her e-mail using POP3 or IMAP. After that she is allowed to send e-mail for a specified amount of time (e.g. 30 minutes). After that she has to retrieve her e-mail again to be able to send more e-mails.

Introduction to mail.tokkee.org

mail.tokkee.org supports both IMAP and POP3. Any user may choose on her own which service to use. Authentication for SMTP (sending e-mail) is available thru ASMTP as well as pop-before-smtp / imap-before-smtp. This howto, however, will only describe howto "setup" up pop-before-smtp and imap-before-smtp. If anyone is able to setup Outlook to correctly do ASMTP, please drop me a note and I will gladly include the instructions.

IMAP vs. POP3

"So..." you might ask, "which service should I use?". Well, I cannot answer this question to you, but I can give you some advantages and disadvantages of both services that might help you make your desicion (this is only my subjective opinion).

Advantages of IMAP:

Fast access as only messages that you actually view are downloaded to your local computer.
Support for many folders.
You can access your e-mail from any computer from anywhere in the world - you only need your connection settings and an IMAP client that's connected to the WWW.
Some IMAP servers (incuding the one running on mail.tokkee.org) already provide means to filter e-mail (sort your e-mails into different folders).
Data on the server is backed up on a regular basis (not yet implemented on mail.tokkee.org - but will be soon).

Disadvantages of IMAP:

You have to be online to access your e-mail (not quite true for all clients as far as I know).

Advantages of POP3:

You can locally (offline) access all of your e-mail.

Disadvantages of POP3:

No server-side support for folders.

Setting up Microsoft Outlook to use POP3

Step 1:

You start by creating a new account. Choose "Tools" -> "Accounts..." in the Outlook menu bar. A new popup window opens where you have to click on the "New" button in the upper-right corner and select "Mail...". A wizard will pop up that guides you thru the basic setup:

[pop3 wizard 01]

Enter your name and click on the "Next" button.

Step 2:

[pop3 wizard 02]

Now, enter your e-mail address. This has to be the complete e-mail address including the domain part. Click on the "Next" button.

Step 3:

[pop3 wizard 03]

Choose "POP3" and set the incoming and outgoing mail server to mail.tokkee.org. Click on the "Next" button.

Step 4:

[pop3 wizard 04]

Set "Account name" to your username. You may also enter your password and activate the "Remember password" option. If you don't do that, you will be prompted for your password any time you log into the server. Do not activate the "Log on using Secure Password Authenticatino (SPA)" option! Click on the "Next" button.

Step 5:

[pop3 wizard 05]

This is the last step of the wizard. Simply click on the "Finish" button ;-)

Step 6:

[pop3 setup 01]

Now we have to do some manuall "fine-tuning". In the top-level accounts window (where you will find yourself after the wizard has finished) choose your newly created account and click on the "Properties" button on the right. A new window will pop up.

Step 7:

[pop3 setup 02]

Choose the "Servers" tab at the top of the window. No changes are necessary here - just double check you don't have "Log on using Secure Password Authentication" and "My server requires authentication" activated (you would need the second one for ASMTP...).

Step 8:

[pop3 setup 03]

Now, choose the "Advanced" tab at the top of the window. Enable SSL for both outgoing mail and incoming mail. Make sure the server port is 25 for SMTP and 995 for POP3. You don't necessarily need SSL enabled for SMTP - however, I strongly recommend doing so as this improves security. The account will not work if you disable SSL for POP3. Now, click on the "OK" button and you're ready to go.

You may now close the accounts window.

Setting up Microsoft Outlook to use IMAP

Steps 1-6:

See steps 1 thru 6 above. Do everything as described above with the only difference that you need to choose "IMAP" in step 3.

Step 7:

[imap setup 02]

Step 8:

[imap setup 03]

Now, choose the "Advanced" tab at the top of the window. Enable SSL for both outgoing mail and incoming mail. Make sure the server port is 25 for SMTP and 993 for IMAP. You don't necessarily need SSL enabled for SMTP - however, I strongly recommend doing so as this improves security. The account will not work if you disable SSL for IMAP.

Step 9:

[imap setup 04]

Choose the "IMAP" tab at the top of the window. Set the root folder path to "INBOX" and the "Sent items path" to "Sent". Now, click on the "OK" button and you're ready to go.

You may now close the accounts window.

Problems

When you connect to the server for the first time after you started Outlook you probably will get a message like this:

[ssl warning]

You can savely ignore this warning. It is caused by me not having signed my SSL certificate by some commercial (and non-free) organisation.

Sending e-mail

After you have set up your POP3 or IMAP account, you can retrieve your e-mail from the server. After that, you are allowed to send e-mail for 30 minutes without any additional authentication. If the 30 minutes are over, simply check your inbox again.

This howto was written by Sebastian Harl (sh [at] tokkee [dot] org). If you have questions, comments or improvements, feel free to contact me.