Do you find the Support WebCast transcripts helpful?
Let us know!

Note This document is based on the original spoken WebCast transcript. It has been edited for clarity.

Heidi Moeller: Hello and welcome to the Microsoft Support WebCast Program. We'd like to thank all of you for joining us today. Our topic is "How to Troubleshoot Sending and Receiving Internet E-mail with Outlook," and our presenter will be Chet Cannon. I'm Heidi Moeller, and I'll be your host for today's session.

We'll start this session with Chet's presentation, and follow that up with a question-and-answer period when the presentation is finished. The Q&A portion of the Support WebCast is intended to encourage further discussion of the topic at hand. However, one-on-one product support issues are outside the scope of what we're able to address during these WebCasts. If you have a product support issue and would like to get assistance, we would encourage you to either phone into technical support or submit an incident on the Web.

With those details aside, let me introduce Chet. Chet Cannon joined Microsoft as a Support Professional back in October of 1998. He has supported Microsoft^® Outlook^® since the release of Outlook^® 98, and has focused on the product for more than three years. Chet currently works for Product Support Services as an Outlook Technical Lead. Thank you so much for joining us, Chet. Let's get started.

Chet Cannon: We're going to start off by touching on areas of connectivity (slide 2), and issues that we run into when we're sending and receiving. The first thing that you need to do is have a connection to your ISP or to your Internet Mail Server. We're going to touch on dial-up networking and virtual private networking connections, or VPN connections. We're also going to talk about local area network (LAN) connections to ISPs, where you would not be dialing out. You may possibly be using a cable or DSL modem.

Connectivity problems can have a direct impact on your ability to send and receive Internet mail. It is important to remember that these problems can spawn from either the client or the server side. So, in the following slides, we're going to give you some troubleshooting tips that will help you narrow down and resolve these types of issues.

On the next slide (slide 3), the first thing we're going to need to know is how to create a dial-up networking or a VPN connection. This should be your first step for establishing a connection to the Internet service provider.

We also need to specify which connection is going to be used for your Internet e-mail service or account. You may have several dial-up networking connections, but you need to know exactly which one belongs with your account. Some providers, when you dial up to them, do require that you use their access number to be able to communicate with your mail server.

Just in general, for creating a dial-up networking or a VPN connection, you should refer to your online help files in Windows^® 98, Windows NT^®, Windows^® 2000, or Windows^® Millennium. If you search on Dial-Up Networking in Help, you will find information that will help you create a connection.

Now we're going to go on to the next slide (slide 4), creating a connection in Windows 95, Windows 98, or Windows NT. You can do this by going to Dial-Up Networking from My Computer. In Windows 2000 and Windows Millennium Edition, you can go to Control Panel to access the Dial-Up Networking component.

A good article to reference here, which you can obtain from http://support.microsoft.com/, is Q138789. That covers how to connect to the Internet with Windows 95 and Windows 98. Now, as far as VPN connections go, we're not really dialing a number. You need to know the IP address or the host name of the PPTP server, and any type of authentication information. So, you need to obtain that information from your company's IT department.

We're going to go on to the next slide (slide 5), troubleshooting dial-up networking or VPN connections. One thing we need to make sure of is that our modem is functioning properly. If you're unsuccessful in connecting to your ISP, try testing another connection, or use your back-up connection. Many times, when you set up software for an Internet service provider, they give you a primary access number and a secondary access number. So, it is a good idea to try the back-up connection.

Also, make sure, in your connection properties, that the correct number is specified. So make sure you're dialing the right number. If there are any prefixes that are required for you to get an outside line, be sure you've set that up. All these things can be set in your dialing properties. When you're looking in Dial-Up Networking on your computer, right-click your connection and go to Properties, and that's where you'll see these settings.

If you're not able to dial up, it's also a good idea to check with your ISP whether or not there are any service outages. If you don't have a connection, you can just give them a call, but most Internet service providers do have some type of service notification on their Web site. So, check with the ISP's Web site, or give them a call to make sure everything is up and running. As far as the modem goes, make sure that you don't have any device conflicts with your modem and another device.

We're going to go to the next slide (slide 6). We covered our connectivity issues when we're dialing up or using a VPN connection. Now we're going to talk about connecting to an ISP over a LAN.

Connections to ISPs can be made over a company LAN without dialing a connection. If you have either a cable or DSL modem, and you're able to connect to the Internet that way, then you would specify a LAN connection versus a dial-up connection. We'll get into the profiles for that a little bit later, but you actually have a choice between selecting a local area network or dialing a specific location, when you're connecting to your ISP.

Now, if you're on a network, sometimes you'll have what's called a proxy server or some type of firewall between you and the Internet. It's important to know if there's any proxy server information that you need to specify when you're connecting to your ISP. Just as an example of a proxy server, Microsoft Proxy Server is a back-end server application that allows you to connect your internal network to the Internet. If you want more information on Proxy Server, you can go to http://go.microsoft.com/fwlink/?LinkId=661.

Some other issues when we're connecting over the LAN (slide 7): you should be aware of, like I said, any proxy server specifications that you need to know to get outside of your intranet to the Internet. To test connections, we can use Telnet. The Telnet command is simply, as you see here on the slides, telnet (space), then the name of your mail server. As an example here, we have telnet mail.sample.com 25.

SMTP uses port 25 to communicate over. POP3 uses port 110. So, if we just wanted to see if we could connect to our mail server, a simple method is to use Telnet. Telnet is going to return something like the name of the server, what type of server it is, what version, and the Internet Mail Services running. You'll see that information in your MS-DOS^® window. So, that's a good way to test if you're able to connect to the Internet.

Some common tools that we can use (slide 8) when we're dealing with troubleshooting, sending/receiving mail, and dealing with communication between our server, are the commands are Ping, Telnet, Tracert (or Trace Route), and NBTSTAT.

On the next slide (slide 9), I have some examples of what these commands would look like if you were running them from the command prompt.

Ping is a very simple command. It is probably the most popular one to use if you're not able to see your SMTP or our POP3 server. And at the command prompt, you would simply type in Ping (space), and the name of your mail server. There will usually be four responses from that address, and that lets you know that you can see the server.

We just talked about Telnet. Telnet allows us to connect to the mail server to see whether or not it is responding to us. So again, that command, which you've seen an example of, is telnet mail.sample.microsoft.com 25; and again, 25 is the port for SMTP; 110 is for POP3.

Tracert (or Trace Route) is a command that will show us how many hops or how many other servers we have to go through to connect to a host. For example, in this command, we see Tracert (space) www.sample.microsoft.com. Now, if we run this from the command prompt, it's going to show you every stop that we had to make before we got to our host. So, this is a good tool to see if we're having any service outages on the way, or if we're getting slow response from some server in our connection to this host.

NBTSTAT is a tool that displays protocol statistics and TCP/IP connections using NBT, which is NetBIOS over TCP/IP.

Back to Tracert, some more information on that. It determines a route taken to a destination. It uses something called the Internet Control Message Protocol echo packets, with varying time-to-live values for the destination. So, it determines the route taken by passages from your machine to a destination address.

As far as connectivity (slide 10), there's another thing we need to be aware of, which is working with third-party dialers. We have Dial-Up Networking, which is a component of Windows. But some ISPs install their own dialer software. It's important to remember that if you are using this type of software when you're under your connection settings for your Internet e-mail service, you need to specify that you're using Internet Explorer or a third-party dialer.

If you run into a problem when you're connecting to the Internet using these third-party dialers, contact the program vendor. If you're using a third-party dialer, you should also make sure the Outlook connections settings are correct.

There are some articles we can reference by going to http://support.microsoft.com/. The first one is Q181599, which is "How to Remove and Reinstall Dial-Up Networking and TCP/IP Files." If you feel that the dialer software that has been installed has damaged your dial-up networking installation, then this is a good article to go through to reinstall everything. The second one would be Q171015, "How to Install and Configure Windows NT Dial-Up Networking." The last article I would reference on this topic would be Q166299, "How to Remove Dial-Up Networking from My Computer." That covers Windows 95 and Windows 98.

On the next slide (slide 11), as far as the connection settings in Outlook, we can set the connection interval for checking new messages. We can set it to automatically dial when we're checking for new mail, and we can also tell Outlook to hang up when it's finished sending and receiving. In Outlook, as far as setting the connection interval, the first place you'd want to go for that would be to Tools, Options, Internet E-mail.

As far as automatically dialing when checking for new messages, you can set most of these values. On the Tools menu, click Options, Internet E-mail. So, if you're following along in Outlook now, you can see where the settings are.

The Connection Interval is just a minute value. You can set it to connect every 30 minutes, or every hour. And Hang up after sending and receiving is important also if you're going to be dialing up to the Internet and disconnecting at intervals, so it doesn't tie up your phone line.

On the next slide (slide 12), we're going to talk about the differences you'll see between the two different versions of Outlook 2000. That's Internet Mail Only versus the Corporate or Workgroup mode. Corporate or Workgroup mode, if you're familiar with Outlook 97, is more like Outlook 97 as far as your connection settings, and as far as setting up your Internet Mail Service. The Internet Mail Only version, is, in essence, more like Outlook Express — you'll notice in that version of Outlook, you have Accounts.

Now the differences between the two, if you can go to Tools, Services in Outlook, that lets you know that you're in Corporate or Workgroup mode. If you can go to Tools, Accounts, that lets you know you're in Internet Mail Only mode. As far as the properties of your Internet mail account, in either version, they're pretty much the same. When you go to Tools, Services in Outlook and double-click on your Internet e-mail account, you'll have General, Servers, Connection, and Advanced, the same as you do in Internet Mail Only.

Here we can set our e-mail address or SMTP and POP3 servers, or the user name and password that we use to connect, and what type of connection it is (whether it's a local area network, or if we're dialing up to the Internet, or if we, like we mentioned earlier, are dialing a third party using a third-party dialer). On the last tab, there's another setting in the Internet Mail Service that will allow you to specify whether or not you want to save messages on the server.

Go on to the next slide (slide 13). We just talked about the Internet Mail Service. Another thing to mention here would be, for instance, the secure password authentication. If there are any MSN^® users out there, this is a setting that you have to specify for MSN. Instead of using just your user name and password, this is an added layer of security for those of you using ISPs that require this. We already covered logon information, and POP and SMTP server names. We'll go ahead now to the next slide (slide 14).

We're going to touch on our settings in the Internet Mail Service. The General tab. I was saying earlier, we have four areas on here. We have to fill out the name you want to refer to these servers by. That could be, for instance, MSN, your name, your organization, your e-mail address, and your reply address.

With the Reply address setting, if you want all of your replies to come to another address of yours, you can specify that here. On the next tab of the Internet Mail Service, you'll see Servers. This is where you specify your incoming mail (POP3), your outgoing mail (SMTP), and your incoming mail server. You have account name and password, and you also have a check box to remember your password. Those are used for connecting over a local area network.

It's important that if you have your account name and password in here, and you want it to just continually check for mail, you need to have Remember password selected and Log on using Secure Password Authentication. And you're also going to have a setting in here for the outgoing mail server. If your server requires authentication, you can specify in your outgoing mail server what user account and password you're using, or you can tell it just to use the same settings as the incoming mail server, or another user name and password.

The third tab you have on the Internet Mail Service is Connection. Here you can select to connect using the LAN, connect using your phone line, or establish your Internet connection manually. You'll also have your properties for the modem underneath here. This is where you specify the Dial-Up Networking connection that you use to connect to your ISP or mail server.

On the Advanced tab, the settings need to stay the way they are, by default. This is where you can specify your SMTP and POP3 server port numbers. You can also specify your server timeouts. So, if you're having a connection problem, you can make the timeout a little bit longer, so it will continue to try and connect to these servers.

You also have, as I mentioned before, Delivery, Leave a copy of messages on the server, and Remove from server after x days. That's a good setting if you're checking your personal e-mail from work and from home. You would want to specify that.

As far as sending mail in Outlook (slide 15) you have three different message formats: plain text, rich text, and HTML. Most of today's mail clients are able to receive mail in these formats. Use plain text, of course, if you're sending mail to anyone who's using an older mail system, which might not be able to receive rich text messages. With HTML, you can send Web pages in Outlook. I just thought I'd let you be aware of the three different types of message formats we can have.

Now we're going to discuss attachments and message content (slide 16). Attachment size is governed by your ISP. So, you should check with your Internet service provider to see what limits are in place for sending attachments. Microsoft recommends keeping attachments to around 1 MB. You can also try zipping your attachments to compress the file and reduce the size of the attachment.

Many of you may have installed, or have seen on Office Update (http://office.microsoft.com/), the Outlook E-mail Security Update. You may run into some difficulty sending attachments after installing this patch. A lot of the new implementations made by the patch are of benefit to you, and we're going to cover some more information about security patch on the next slide.

TNEF (Transport-Neutral Encapsulation Format) is important as far as attachments go. TNEF is a proprietary method for encoding RTF messages that are sent across the Internet. A TNEF-encoded message contains a plain text version of the message and an attachment that contains the RFT version or the Rich Text Format — any objects such as pictures or other attachments that were sent with a message. When a message containing TNEF information is received by a mail client that does not understand what TNEF is, an attachment is created with the name Winmail.dat. In some cases, the mail server looks for and strips out the TNEF information and the Winmail.dat information.

Some of you may also run into some difficulties with the message body being received as an attachment. For instance, if we were sending a page in the body as HTML, and the recipient received it as an attachment, then you might want to specify that you're using rich text to send to the recipient. You can do so by opening up your contact, double-clicking on their e-mail address, and then forcing it by selecting the check box that says, Send to this recipient in rich text format.

Now we're going to discuss the Outlook E-mail Security Update (slide 17), and we're going to answer a couple of questions, as far as how it protects you. Can you customize a security patch? What can you do if you've installed the patch and you still need to open up a received attachment?

The Outlook E-mail Security Update increases the level of security in Microsoft Outlook by limiting certain functionality. Attachments that can contain executable code are unavailable within Outlook and the Outlook E-mail 2000 Security Update installation.

As far as the attachments, they are broken up into two different levels, Level 1 being a category that includes extensions that might have some script or code associated with them. Any attachment with an unsafe file extension is inaccessible if you use a version of Outlook that has a security patch applied to it. There are a number of file extensions on the Level 1 list — executable (.exe) files, as an example — that may be considered unsafe.

There are Level 2 files, which are considered unsafe. They do require more security than other attachments. When you receive an attachment that's categorized as Level 2, you may be prompted to save it to disk rather than opening it inside of the application. You cannot open the attachment from within the message. By default, there are no file extensions associated with this group. However, you can add file extensions to this Level 2 list. If you're in an Exchange server environment, this will differ a little bit. There are some more changes that can be made by the administrator.

Microsoft expects that customers will need to access attachments and have the ability to share information from a trusted source. Given this, there are a couple things you can do. You can zip the files using any program available on the Web. There are several popular ones for compressing files. Zip the attachments that you have to send, and send them to your recipient. When the recipient gets them, and if they have the same program on the other end for unzipping the file, they'll be able to open up these attachments and then get the data from a trusted source

Another thing is you could try sending a link to a file server or a Web server rather than attaching the file to a message. That's going to be a lot safer, because we'll be going out to another location on the Web, and again, just in general, you're making sure that this information is coming from a trusted source.

Now we're going to touch on troubleshooting. We're going to go over some different error conditions that you might have run into (slide 19). The first one here is "The server could not be found" or you're "Unable to connect to the server." Just in general, it's a good idea to go in and check your account settings based on what your ISP has given you — your SMTP server name, your host name. You can try ping, as we mentioned earlier, to see if you can actually find the server.

Another one is "TCP/IP connection was unexpectedly terminated by your mail server. If this problem persists, contact your LAN administrator or Internet provider." If you run into this, we could be dealing with an issue where there are too many inbound connections to the SMTP server, which means we have too many people connecting to that server at this time. If you're not able to send e-mail currently when you're running into that type of error, you might want to just try sending the message later.

When you're sending an e-mail attachment from Outlook, you might lose your connection to your ISP (slide 20). If this happens, again, we could be dealing with something where there could be too many connections to the mail server, or your dial-up connection was dropped off. So, if you run into that error, make sure that you're still connected to your Internet service provider.

With the next error, when we're sending e-mail messages with attachments over the Internet, recipients report that the message may contain an attachment called Winmail.dat. If you receive this message, or if your recipients complain that they're getting an attachment called Winmail.dat, you might want to try using the plain text mail format to send to these recipients. So, in Outlook, you would go to Tools, Options, Mail Format, and switch it to Plain Text.

Some other errors that we'll run into (slide 21): "Could not send the message." Here, again, we could be dealing with a problem with your mail configuration. So, it's a good idea to check your account settings, or there could be a problem with your message store.

When we're using Outlook to connect to an Internet Mail Server, we're going to be using a personal folder to store our e-mail, contact information, etc. It's a good idea is to create a new personal folder. A couple of Knowledge Base articles for reference here would be, first, Q195717. This shows you how to create a new personal folder in Corporate or Workgroup mode. For Internet Mail Only users, you can reference Q195723, "Creating a New Personal Folder for an Internet Mail Only Account."

"Unable to send this item." Again, we could be dealing with configuration. It is very important, when we're running into errors like this, to make sure that we have the right SMTP server and the right POP3 server in there. We could also be dealing with a problem with the personal folder message store. So, a couple of other articles to reference here would be Q195714, which is "Troubleshooting Outlook Configuration Problems in the Internet Mail Only Mode," and Q195795, "Troubleshooting Outlook Configuration Programs in Corporate or Workgroup Mode."

"An unknown error was returned from the SMTP server." Here, we're dealing with a problem where you're logged on to your Internet service provider and you're trying to send e-mail through another ISP's SMTP gateway. So, this error might be received if you're accessing the Internet through a dial-up connection, through a cable modem or ADSL, or through a LAN.

It could also be that there's a problem with your ISP's SMTP server. This would be a good time to give your ISP a call to check if there are any service outages in your area. This can also be caused if there are any invalid characters or spaces in your computer name box. To check on your computer name, you go to your network properties, which you can get to by going to either the Control Panel or right-clicking Network Neighborhood from your desktop.

You can also get this error if your message or attachment is larger than the ISP allows. Your ISP will be able to provide you information as far as maximum attachment sizes. So, check with them and see what their maximum allowable attachment size is.

"No transport provider was available for delivery to this recipient." This is commonly referred to as an NDR, or non-delivery report. This can be caused for a number of reasons, such as a damaged personal folder. With Outlook 2000, we do require the installation of Outlook Express. If you get this error, you could be running into a case where Outlook Express is damaged, or it has been removed. So, make sure you have Outlook Express installed on your machine.

"No mail transport service in the mail profile." You can also see this error if you haven't properly set up your Internet Mail Service in Outlook. It could be a damaged contact, or you might also be dealing with an issue where the mail server is expecting the address to be enclosed in angle brackets, or the mail server doesn't recognize your IP address. So, I would also work through your troubleshooting configuration problem article (Q195714 or Q195795) in regard to this, or just refer to the article I mentioned earlier, regarding creating a new personal folder (Q195723).

Now the last thing here, "Mail remains in the Outbox after performing a send and receive." This would be a case where you compose a message, send it to some recipients, and it stays stuck in the Outbox. If you run into this, you might be facing a damaged personal folder. Your Personal Address Book could be damaged. You might have an outdated or incompatible add-in. It could be that you replied to an e-mail message that was received from an old Internet mail account.

It's a good idea to first try resending the message. Make sure that you have the correct e-mail address for the person you're sending to. Make sure that you're not working offline, and have not made a remote connection. The other thing it could be was you opened the message from your Outbox before it was sent. So, as far as working offline, if you're in Internet Mail Only mode, go to File and clear Work Offline.

On the next slide here (slide 22), I have included some good articles that will help you out when you're dealing with problems in Outlook; Outlook troubleshooting articles for both Internet Mail Only and Corporate or Workgroup mode are referenced. If you want some more detailed information about the Outlook E-mail Security Update, you can look at this article, Q262631. And there's a link to the Outlook Web site (http://www.microsoft.com/outlook/).

If you have any product suggestions or feedback, please feel free to e-mail us at outwish@microsoft.com. Let's open it up for Q&A; at this time, I'll hand it back over to Heidi.

Heidi: Thanks very much, Chet. It is time to start the Q&A portion of this Support WebCast. The Q&A portion of the support WebCast is intended to encourage further discussion of this topic. However, if you need one-on-one product support, we encourage you to go and get some assistance either by phoning into Product Support Services or submitting an incident on the Web. One-on-one product support issues are outside the scope of what we can do during these broadcasts.

We have had several questions submitted so far, so I'm going to get started. The first question is: With regard to DBCS message testing, Internet messaging has often caused unreadable characters, especially in double-byte character sets (DBCS) languages such as Japanese, Korean, and Chinese. Our company is getting ready to test Exchange 2000. Is there any testing suite that we can use to ensure that the Exchange 2000 implementation is successful in supporting these languages?

Chet: That would probably be a question best answered by Exchange product support. I know that we have some. We have a couple of Knowledge Base article on DBCS, but I would direct that question over to the people in Exchange.

Heidi: Chet, you specialize in the Outlook side, and there are different engineers who specialize in Exchange support?

Chet: Correct.

Heidi: I did get a few people asking you to repeat the Q articles that you listed during the broadcast. You listed one early on, and then two more a little bit later. I don't believe that these were referenced on that last troubleshooting slide.

Chet: I can go back through those. The first one I referred to was how to connect to the Internet. It's a good article for users of Windows 95 and Windows 98, and that is Q138789.

Heidi: What about the other two? I caught one of them. It was Q171015

Chet: We were talking about dealing with third-party dialer issues. I gave you three articles to look at: Q181599, "How to Remove and Reinstall Dial-Up Networking and TCP/IP files"; Q171015, "How to Install and Configure Windows NT Dial-Up Networking"; and Q166299, "How to Remove Dial-Up Networking from My Computer."

Heidi: Now we have all those listed. The next question is: Can you touch on troubleshooting low-level problems authenticating the remote Outlook client against the Exchange server at profile setup?

Chet: In today's session, we were discussing Internet e-mail, but when connecting to an Exchange server, it's also a good idea to try pinging the server. Ping comes in handy to check if we're able to see that server sitting out there.

If you're using an older version of Outlook, another thing you can try is the old Exchange client — try testing another client to see if you can connect the Exchange. If you're using Outlook 97 or Outlook 98, and you're running Windows 95 or Windows NT, you can start the old Exchange client by clicking Start, Run, and typing Exchng32.

If you're unable to connect to the server, another thing you could try, instead of using the host name, is using the IP address of your Exchange server. If you don't know the IP address, you can use the Ping command, and when you get replies from your Exchange server's host name, assuming that we're able to communicate with it, you'll be able to see a reply from the server's IP address. You can try specifying the IP in the Exchange server host name, rather than putting in the host name.

Heidi: Moving on to the next question: What is the best way to troubleshoot the "No transport provider was available for delivery of this recipient message" after you have verified that the account host exists and other Internet mail is getting in and out?

Chet: For "No transport provider," we could be dealing with a damaged personal folder. There were a couple of possible problems I went over, including damaged Outlook Express files. Outlook Express is an integral part, and there are some files shared between Outlook and Outlook Express. So, it is important that we have Outlook Express installed and fully operational on the machine.

Go back through your mail service configuration. Make sure that you have all the correct settings in there. You could be sending to a damaged contact, or you might have an apostrophe in your computer name. You could also be dealing with an issue where you need to be using SSL authentication, and you're not configured properly for it.

No delivery or address type for the Microsoft mail service, which I mentioned before, where the mail server just doesn't recognize your IP address. And no transport provider. One article you can reference there would be Q197417.

Heidi: Before we move on to the next question, I do want to encourage all of you to take a few moments to submit some feedback, using the feedback@microsoft.com alias. We are very interested in your feedback regarding the Support WebCast program overall, any comments you have about this topic, or any suggestions for topics you'd like to see in the future. On to the next question. This looks like it has to do with Exchange server as well, but we'll see if we have an answer here. What tools would you suggest to test connectivity to a Microsoft Exchange server that is behind a proxy server?

Chet: As I mentioned before, Ping is going to be a good one. If the Exchange server is behind the proxy, then we're going to be either dialing up to it, or perhaps using a VPN connection, as I discussed earlier. Again, if you're using VPN or something like that, it's always a good idea to check your connection settings.

There's a file on your machine called Host. Make sure that Host does not have an IP-to-host name mapping for your Exchange server. That could run you into an issue where if your server IP address is already mapped out in the Host file, the Host file is going to be looked at first in naming resolutions. So, if you have an entry in there for it, you might want to just remove it, so it can be dynamically resolved.

Just in general, you can also use Telnet to connect to your Exchange server, by typing Telnet (space), host name (space) 25, or 110 if you're connecting to Exchange, POP3, or SMTP.

Heidi: Thanks, Chet. Moving on to the next question: With regard to Outlook Express versus Outlook 2000, why won't some attachments flow to Outlook Express?

Chet: I guess they're saying they're not able to receive the attachment in Outlook Express, but they are in Outlook?

Heidi: That's what it sounds like to me. That hasn't been clearly articulated, but that is what I would guess is the gist of it.

Chet: We probably need to know more specifics about that type of issue, as far as what kind of attachment they're sending. Just in general, it's always a good idea to go through and check the account settings again, and make sure that you're using the proper account settings. If you're still receiving mail and you're just not getting the attachment, you may want to try sending attachments through to yourself, to see if you can receive them on the Outlook Express side.

There's one thing to note though, with using Outlook and Outlook Express on the same machine: When you connect to the same mail account with both clients, On the Tools menu, click Options, click Advanced, and select Leave a copy of message on the server — a pretty common issue we'll run into is a person will have a machine at home, and a machine at work, and both are connecting to the same mail account. If they don't have Leave a copy of message on the server selected, then whichever e-mail client, Outlook or Outlook Express, gets to the message first, it's going to download it and mark it as downloaded, and when the other client goes to retrieve messages, it won't be there. So, it's important that you have that setting specified in your mail account so that these messages will stay on the server. And you can also set it to remove the messages after x number of days.

Heidi: Moving on to the next question: Why would my Outlook 2000 only show two formats for e-mail, plain text and HTML? It sounds like rich text is not showing up.

Chet: If you are in a workgroup and Outlook 2000 was administratively installed on your machine, and that's what really sounds like is happening, I would check with your system administrator to make sure that this setting was not purposely turned off. There is a registry key that you can use to enable or disable the setting. But it is probably best that we go through your system administrator to make sure that they haven't turned that off on purpose.

Heidi: Next in line: Why is it some people cannot get an attachment if I have rich text selected in Outlook? That seems like it almost might tie into the last question, doesn't it?

Chet: Sort of. We covered that — for instance, the Winmail.dat. A good thing to try doing, if these recipients continually don't receive your attachments, is to try sending in plain text. That also goes back to another topic we discussed, which was the Outlook E-mail Security Update. If you're sending any attachments to these recipients that occur on the list of Level 1 attachments, the attachment will be blocked out. So, a good article to reference for more information about the security update is Q262631. In this case, any of these files — an .exe, a .com file, anything like that — the Outlook E-mail Security Update will strip it out of message. So, those recipients will not receive that.

Heidi: The next question: With regard to using digital certificates, can you give some advice on options for sending messages signed by digital certificates specifically using clear text signatures and compatibilities with mail clients other than Outlook?

Chet: We do have some information on that. Here are a couple of articles to reference:

Q198184 "OL2000: (CW) Features Available with Microsoft Exchange Server."

Q195477 "OL2000: Encryption and Message Security Overview."

Heidi: Let's hit the next question: What do you do when you have a message with an attachment that freezes Outlook?

Chet: I would first probably need to know what kind of attachment it is, and if it's freezing the client, it may be that there's a problem with the associated application. Ensure that, whatever type of file attachment it is, the program that opens it is working properly. Also, that sounds like it could possibly be, just with the information I have, something malicious.

Ensure that the program that the file is associated with is functioning properly, and just be wary of the source of the message, to ensure that it couldn't be anything with malicious content.

Heidi: Sometimes I send in an attachment by Outlook, and when the receiver gets the message, he can only see the attachment as symbols. It doesn't look like an attachment any longer. Do you know why this would happen, and what I can do to solve this problem?

Chet: This is similar to what we were talking about the Winmail.dat. There are also other cases where people will receive cryptic attachments that don't really make any sense. I would try, again, sending to the person in plain text format. If you ever have problems sending attachments to anyone, it's always a good idea to step your message format down to plain text and try sending the message out that way.

Heidi: Does Hotmail^® or Yahoo accept HTML or RTF? Do you happen to know that?

Chet: I believe Hotmail does work with HTML.

Heidi: Moving along to the next question: With regard to technologies for encryption, can you tell me what some of the newest technologies for encryption of e-mail are? And do you have any suggestions for which ones I should use?

Chet: Not to make an endorsement, but Verisign is out there, the Web is a good place to obtain information about it. In general, I don't really have anything prepared for that question, but use the Internet; I would search for different encryption technologies. But Verisign would probably be our first reference point for those types of security.

Heidi: It sounds like there are a lot out there. I know we are not able to recommend a specific vendor, but you said Verisign is one that's available.

The next question is: How do you know when to use plain text versus RTF or HTML?

Chet: You're not going to know right off. If you don't know your recipient and don't know what e-mail program they're running, it's just a good idea to try to sending the message in rich text to start off with. There's really no way, before you send a message, that you're going to know whether or not this recipient can read it, unless, of course, you know who the person is. So, I would always try testing, and sending in rich text format.

One thing I wanted to mention, and I didn't bring it up earlier, is that when you're using the Internet Mail Only version of Outlook, it always sends in rich text. If you want to send a message to a recipient in plain text only, in Internet Mail, you have to go to the properties of their address and specify to Send E-mail in plain text only.

On the flip side of that, with the Corporate or Workgroup mode, if you want to send RTF to a recipient, you need to open up their contact, go to the properties of their e-mail address by double-clicking on it or right-clicking it and going to Properties, and saying to Always use rich text.

Heidi: The next question: With regard to the Outlook patch that you mentioned, I'm unclear about this: If the patch is applied, did you say you cannot send or receive attachments? If that's the case, what's the alternative?

Chet: I discussed levels of attachments, Level 1 and Level 2, and if you look at article Q262631, that's going to give you a list of file attachments that are inaccessible in Outlook, if you have a security patch applied.

Now, if you have someone that you're sending mail to, or you're receiving mail from, and they are a trusted source, and the data is not malicious, then you can try zipping up the data files or Word documents, whatever it might be, into zip files, using a number of different popular compression programs that are out there. WinZip is one program that you could use to do that. But if the file is zipped, you'll be able to send that zip attachment successfully through, because that is not on our Level 1 list of file attachments that are inaccessible.

Heidi: Moving on to the next question: In Corporate or Workgroup mode, is it better to send using SMTP in both directions, or to use the POP3 connector for Exchange Server 5.5 SP3?

Chet: I guess I'm a little unclear on that question, but if we're using Exchange Server service on the profile, that works a little bit differently than the Internet Mail Service. But if we're connecting to the Exchange server that is configured for POP3 and SMTP access, you would want to specify the correct host name for your Exchange server in both of the POP and SMTP fields. And with Exchange server, you would just have one field where you specify the name of your Exchange server.

If you would like to get a little bit more information on that, I'll need some more specifics from the questioner. So, please take down their contact information. I'd like to get back to them.

Heidi: If the individual who submitted that question could send some additional clarification based on what Chet has just said, we can certainly look at that question again, in just a few moments.

Let's go on to the next question: Why is Outlook Express required for Corporate or Workgroup mode? It seems to confuse users.

Chet: There are a number of files in there, as far as the ability to read HTML mail, and some security settings, that are shared across the board. Outlook Express is a required component of Outlook 98 and Outlook 2000. It's also the newsreader for Outlook 98 and Outlook 2000. So, those are the reasons why. Maybe you have a lot of users out there that will use Outlook for their information management, where Outlook Express is just a simple mail client where you still can maintain a contact list, but it doesn't have all the features of Outlook.

We basically just have some shared files there. If Outlook Express is not present on the machine, you can expect to run into some problems with Outlook.

Heidi: Moving on to the next question: With regard to capabilities of an Internet Mail Service provider, what is the best way to determine ahead of time what the capabilities of an Internet Mail Service provider are, so that you find out before your recipient complains? Is there an Internet table somewhere, or some sort of good test message to send?

Chet: That's a good question. I'm not really sure if there's a resource on the Internet that would give us that type of information about different ISPs. Of course, you're going to see from time to time reviews in magazines, etc. If you're trying to decide which ISP to go with, I would say the best thing to do is go to the Web and do a little bit of research. I'm sure you can find some information on customer satisfaction, etc. But most of that would probably be available on the Web.

Heidi: Typically mail services are offered by your Internet service provider, correct?

Chet: Correct.

Heidi: So would that Internet service provider also typically have information if you phone them, and be able to tell you what the limitations are of their mail service?

Chet: Sure. I'm sure that's a question that any ISP's support people will be able to answer. Yes. I would say it would probably be advisable, if you had some questions, to give them a call or shoot them an e-mail.

Heidi: Next question: With regard to Net Folders: Can you talk just a little bit more about Net Folders? The question is a bit broad. So, maybe just touch on what Net Folders are, and do a quick overview. Is that possible, Chet?

Chet: Sure. I can do that. Actually, we delivered a WebCast on that a while back (http://support.microsoft.com/servicedesks/webcasts/wc011800/wcblurb011800.asp). But Net Folders is a way for you to be able to share information via e-mail with your coworkers. You can go in and share a folder, such as your Contacts folder.

Now, when we were talking about rich text and making sure people can receive it, that's a key part of Net Folders. If you cannot send a rich text message to one of the people that you want to be a subscriber of yours, then Net Folders is not going to work. So, a good thing to do would be to send a meeting request, as an example, to one of the people you intend to share with. If they're able to receive the message and see the buttons for Accept and Decline, then we know we have rich text up and running.

But Net Folders, not to get too far off the subject, lets you share one of your folders — Contacts, Calendar, Inbox — with another person, and you can assign different levels of permission, such as whether or not you want them to be able to contribute to the folder, or just to be able to read the information in the folder. Net Folders does not work with Exchange Server information stores. You would have to use a personal folder when you're sharing information with Net Folders.

For more information about that, I'm going to refer you to an article here for you on Net Folders to give you an overview of what it is, and what you can accomplish using it. Refer to Q179509 for Outlook 98 users, or Q195867 for Outlook 2000 users. Net Folders does work across versions. So An Outlook 98 user can share with an Outlook 2000 user, and it works between Corporate or Workgroup and Internet Mail Only modes.

There are a lot of things that you really need to know before using Net Folders. When I was discussing Internet mail and being able to send rich text, a lot of those questions are answered in Q229962, for Outlook 2000 users. For Outlook 98 users, it's Q196297. And this feature is not available in Outlook 97.

Heidi: On to the next question: With regard to slide 9, you mentioned NBTSTAT. What is this command used for again? I did not catch it.

Chet: NBTSTAT displays the protocol statistics, and it shows current TCP/IP connections that we have open. If you run NBTSTAT, you'll be able to see what type of connections are currently open. There are a number of different switches that you can run, and it will give you some more information.

It's useful in any network where IP addresses are dynamic. So it's not really a good tool to test just to see if you can hit the server, as Ping and Telnet are, but it's certainly a useful tool when you're going to just look at protocol statistics to see what connections you have using the TCP/IP connections that are open.

Heidi: Moving on to the next question. This is one that is a little bit outside the scope, but I'm going to go ahead and ask it just in case: You mentioned something about doing some Telnetting to do some testing of commands. This individual is asking if you could give them some Telnet commands to help in troubleshooting via Telnet, besides trying to log on. Is that something that you have information about?

Chet: You're probably going to find better resources on the Web. If we did telnet pop.sample.microsoft.com 110, you would then get a response back from the server. At this point, you would be able to issue the User commands by typing in User (space) your user name and ENTER. And then next, you would use the Pass command, which would be Pass (space) your password. That gets you on to the server.

I really don't have a lot of information on it. It's probably best that you look at the Web for that information. Telnet commands do differ, in some cases. So, depending on what your ISP is running on their back end for the mail server, you probably want to look to the Web as a reference for commands.

Heidi: Once again, this is leaning toward product support, but I'm going to ask it just in case you have a quick solution: How would you troubleshoot an occurrence of forwarded mail arriving without body text being included?

Chet: There are some options in Outlook 2000when you're forwarding mail. If you go into Outlook and you click Tools, Options, Preferences, and select E-mail Options, from here, you have some settings for when you're forwarding a message. If you look at E-mail Options, you'll see On replies and forwards, you have some different things you can specify there for forwarding: including original message, including and indenting their original message text, attach original message, and prefixing each line on the original message included.

Now, if you're forwarding a message, and no text is coming over, then it's probably going to be something that we'd want to take another look at, to get some more information from you, so we can troubleshoot that issue better. You can also try, if you're running into a case where it's not sending, switching your message format between plain text and rich text, and you may also want to go to the properties of your contact's e-mail address to make sure you specified rich text.

Heidi: Before we go on to the next question, I just wanted to make a note here. I have had some additional questions sent in specifically regarding Exchange, questions about how to do things in Exchange and on troubleshooting Exchange. We will not be asking those questions during this session. Unfortunately, that is outside the scope of the Support WebCast. Our focus today is Outlook. So, if you do have questions specifically regarding Exchange, I would encourage you to either phone in for product support if you need assistance, or submit an incident on the Web, or possibly find some additional information on Online Support.

The next question is: How can I expedite the deletion of messages, and that whole process, if a user cleaned up the Inbox, but the files are still in the information store. How can we manually clean them up in the information store?

Chet: An information store — I'm assuming they're referring to personal folders. I think what he's asking is, if you selected a lot of messages and deleted them, why doesn't the size of your personal folders appear to be reduced? If we have a personal folder that's 2 MB, and you delete 1 MB of messages, you might notice that the size is still up there.

One thing you can do is go into the Properties of your personal folder. If you go to Tools, Services in Corporate or Workgroup mode and go to Properties, your personal folder, you have an option for Compact now. Now, in Internet Mail Only, you would go to your folder list, right-click on Personal Folders, and go to Properties to get to this. But I would say, if you're noticing the size is not decreasing, try clicking Compact now to see if that helps reduce the size of the file.

Heidi: Moving on to the next question: Is it possible to randomize signatures in Outlook 2000?

Chet: With Outlook 2000, I can specify different signatures. I can create a business signature, or a personal signature, if I like. I can change those signature settings by going into Tools and Options, and going to the Mail Format tab and clicking on the Signature Picker.

Now from the Signature Picker, you can create new signatures and save them, and you can go back in here to Tools, Options, Mail Format and change your signature. In Word, you can go in, if you're using Outlook 2000 with Word mail enabled (and to enable that, you go to Tools, Options, Mail format, and click Use Microsoft Word to edit e-mail messages) and create signatures as well, and you can switch those on the fly.

If you open up a new message, your current signature is displayed. You can right-click it from there to change the signature that's being used. Using Word as your e-mail editor, you can make that change to your signature a little bit more on the fly, without having to go through Tools, Options, Mail Format.

Heidi: The next question is: What is the difference between VPN and DUN? Can you use VPN with DUN, or are they separate? Does it make a difference, as far as security is concerned?

Chet: To create a VPN connection or a dial-up networking connection, we're pretty much going to the same place. If we're creating a virtual private networking connection, all we're really going to need to know is the host name. So, if your company's administrator has set up a server to handle these types of requests, you need to get that information, and the authentication information.

With a VPN connection, you're not actually dialing. You're not using the modem to connect, as you would be with a dial-up networking connection. So, those are the two core differences.

If you are dialed up to the Internet, you could still dial a VPN connection to give you access to another network, if that answers your question. So, yes, you could use dial-up networking to first establish a connection, to one network. Then you could use VPN. You could connect to another VPN connection, and go to another network.

Heidi: Next in line: Why does Outlook 2000 look for a program named Liv.exe when attempting to open an image, a .jpg, a .gif, or a .bmp? It is not the default viewer for the file type; how can I change it? I don't know if that gives you any additional information.

Chet: I'm not sure what Liv.exe is, but to change which program opens up a certain type attachment, you can go to Windows Explorer, and that's either by going to Start, Programs, Windows Explorer, or Start, Programs, Accessories, Windows Explorer, depending on the operating system. And then you would go to Tools (or View, in Windows 98), Folder Options, click the File Types tab, and from the File Types tab, you're going to have an alphabetical list of registered file types. A GIF file, a JPG file, all these different types will show up here, and there's a program that's associated with them.

For instance, probably all of you would have a .gif image on your machines. Down at the bottom where it says Opens with, mine is currently set for Microsoft Photo Editor. So if I select GIF Image from the list, I can then click Change (or Edit, in Windows 98) so that file type will open up in any type of program I choose that's able to open those images. That's where you would go to change your file associations.

Heidi: The next question is: Can PKI be used for encryption?

Chet: PKI, I'm not familiar with that.

Heidi: Public key infrastructure.

Chet: You're just wondering if those can be used for signing e-mail messages? Was that the question?

Heidi: It doesn't say specifically signing e-mail messages, but I'm assuming that's what it's in reference to, is if using PKI can be used for encryption within Outlook.

Chet: Yes. You could. You can do that. I believe there is an add-in. I haven't played around a lot with that, but I believe there's an add-in in Outlook for PKI. So yes, if you have a signed message, you can use that to open up messages.

These are some links that will refer the customer to companies that develop PKI encryption functionality for mail clients:

• http://www.globalsign.net
• http://www.sse.ie/trustedmime.html
• http://www.slipstick.com/addins/security.htm

Heidi: Next in line: Why can't we send large, for example, 1 MB and up, .jpg attachments to clients without causing their e-mail to freeze? Once again, this sounds a little bit like it might be a support issue, but do you have a couple of quick comments on that, or is it really going to take some more probing to find that out?

Chet: It sounds like the recipients are getting the message, but then when they try to open this attachment — I don't think it's a problem with the size, because it sounds like it's actually getting to its destination. The message is being received. When they're going in and opening up the attachment, that's when they're running into the freeze.

That could, again, be the program that's associated with that file type. It might be that they don't have anything registered there, or that the program that is supposed to open that file type is having some problems. If that's not the case, you might want to consider opening up an incident with support.

Heidi: The next question: Can you get around sending Level 1 attachments, or I guess the inability to send Level 1 attachments, by removing the file extension?

Chet: I guess that's similar to the workaround I mentioned with zipping the file, in essence — that would probably be just as effective. If you go in and rename the file types, and then the person on the other end knows it's coming from a trusted source, then you could do that. But as far as getting around the patch with the list of Level 1 attachments that are there, that cannot be done.

Heidi: The next question is: What is the best way to compact a mailbox? When a mailbox is full, the user can delete a lot of messages, but the information store is still the same. I'm once again thinking this is the local mail store.

Chet: If they have a rather large .pst, and they've done the Compact now, and they still don't notice the size decreasing, it might be a good idea to try exporting the .pst, by going to File and Export. Export it out to another .pst file, and see if you notice a difference in the size. The file could be damaged; a good tool that you have for that situation is the Inbox Repair Tool.

You would get to it by going to Start, Programs, Accessories, System Tools, and Inbox Repair Tool. Now, that will be available in Outlook 98 and 97. It's a good tool to use to determine if there are any problems with the file.

As far as it fixing the file, unless you get an error that specifically says you need to run this tool, then I would say it's probably not going to be able to diagnose and fix every problem. But if you get the error, in most cases it will repair the file.

Heidi: The last question it looks like we have at the moment is: What is large for a .pst file: 200 MB, 300 MB?

Chet: The limit of the .pst is 2 GB. So, if we get past the 2-GB barrier, then a .pst is going to be virtually unusable. It's a good idea to make sure that you keep the information store and everything healthy. If you start approaching a pretty large size, it might be a good idea to archive, and you have archive functionality built into Outlook. If you haven't used the archive functionality before, just see the online help in the program. But archiving is definitely a good practice.

We don't archive Contacts and things like that, unlike Calendar messages, which would expire in time. We don't archive Contacts. But any information that you can move to a backup .pst, it might be a good idea to do that, if you're approaching that 2-GB limit.

Heidi: With that question answered, we have cleared the queue of all the questions that were submitted during today's broadcast. I do hope this content was useful for you, and that you find time to join us again in the near future. We do have a session just about every Tuesday and Thursday and some Fridays. Typically it's 10:00 a.m. Pacific time, although we might start varying those times a bit.

If you're interested in seeing the content that we already have available, we've done about 150 sessions so far that we have archives available to. You can go to the URL I pointed you to, http://support@microsoft.com/webcasts/. At the bottom of the page, you'll see a link to Past WebCasts, and from there, you'll be presented with a page that has a list of all of the various technologies we cover, and within that, we have listings of all the sessions. Once again, thanks so much for joining us today. Have a great day. We hope to hear from you again in the near future. Thanks, and good-bye.