Vexing Email Troubleshooting

Most of yesterday was spent trying to help a friend troubleshoot a vexing and perplexing email problem at his office.

The friend owns a small business selling industrial equipment. Almost all of his transactions these days are conducted via email or faxes, with web access being very important also. When his fax line, email and web access stopped working properly, it interrupted his business big-time!

The exact chronology of the problem has been lost in the mists of time, but last Friday, he began to have problems sending email. Thinking the problem might be temporary, he left things alone over the weekend and figured he'd take care of it Monday morning. No such luck...

He has worked on this problem with:

• The ISP via the phone and in person at their office
• The telecom via the phone and a serviceman's visit to his office building
• A serviceman from the company that installed his phone system and came to the office to check things out
• Luke W and myself

He also bought a new router because it seemed to be dead. When he went to the ISP office, they tested his router and modem and said the router was dead and the modem was ok.

He has now spent the better part of four and a half days trying to get someone to help him get his fax to be able to send and receive, his email able to send and receive, and his computer able to access the web. The phone line, fax and web access were finally fixed today, and the rest of the day was spent on email. Neither Luke nor I were able to make Outlook Express send out emails, although it receives them fine. As a stopgap measure, Thunderbird was installed on his computer today, and it seemed to send emails fine. But later tonight when he tried to send a Thunderbird email with an attachment, it was only able to send very small attachments. Large attachments stopped T-bird emails in their tracks. A problem page on the web related to large attachments for T-bird listed several possible solutions. All were tried except using a different SMTP mail server. None of the listed solutions helped.

In between adjusting various settings on Thunderbird and researching potential problems/solutions on the web, an attempt was made at 9:30 p.m. to send email using Outlook Express, something that had not worked since the internet became accessible this morning around 10 a.m. Surprise -- Outlook Express sent an email just fine. One more was sent, then two more just to make sure it wasn't a fluke. But when my friend sat down to try sending one with Outlook Express about five minutes later, it had reverted to not sending out emails.

There's no way something this simple should take this long to troubleshoot. But it has, and it continues to drag on. Small examples like this show how much the internet has changed the way America does business, and how much trouble it would cause if the internet developed major problems for weeks or months. Scary...

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