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With some ISPs devaluing dialup in favor of broadband, there are many reasons dialup might start to get slightly more problematic over time.
When I am trying to connect via my dial up modem, I have to try several times until the modem responds and starts screaming with the handshake. This problem evolved over time and in the beginning of using the modem, there was no delay to get the connection. This happens in Outlook Express as well as connecting from the desktop via the network connections.
So, I am assuming that there is something wrong in the software making the connection. Any advice would be appreciated.
Actually, that's not at all the assumption that I would make.
I'm thinking that the software's probably just fine, but that the problem lies elsewhere - in the modem, the phone line or the ISP.
Let's look at each, and how a software setting or two might help diagnose.
Nine times out of ten the problem you describe is due to something very, very simple: a busy signal.
With dialup modems becoming less and less common, ISPs are likely cutting back on what's called their "modem pool" - the number of available modems they have at their end to receive your call. If those are all in use by other customers at the time you call in, then you'll either get a busy signal, or no answer at all. With most computers set to remain silent when you dial in, you'd never hear this.
However, Windows should eventually time out and tell you "no answer" or "busy". So be sure to let Windows keep trying until it gives up and reports the error.
There are two other quick ways to diagnose this being the issue: when it happens, immediately pick up your own phone and dial the modem number. If you hear a familiar busy signal, or continuous ringing, you'll know this is the problem. If you hear a high-pitched tone (called the "answerback tone"), then a modem was available and the problem likely lies elsewhere.
Another option is to investigate the settings for your modem in Windows to enable the speaker during dialing. Available on most modems when you turn the speaker on you'll actually hear the modem dial and you'll hear the response - be it answerback, busy or no answer.
One other thing to try is to use a different phone number to dial in to your ISP. Many if not most ISPs that provide dial-up service actually do so via several different incoming phone numbers. Sometimes those route differently or to different modem pools. It's worth a try to see if this makes a difference.
If we assume that the problem is not the ISP's availability, we move on to other ideas.
Dial-up modems depend highly on the sound quality of your phone line. Typically noise is what makes the difference between a 22.8kbps connection versus a higher speed. In the worst case, the noise can be bad enough to prevent the modems from making that initial connection.
The reason I don't think this is what you're experiencing is that normally this would result in that handshake you do hear going on for a long, long time until your modem finally gives up.
There remain other less likely possibilities:
Your phone company could be having capacity problems and are unable to connect your call. Again, configuring your modem so you can listen to the dialing sequence would help diagnose this. It's likely you'd experience this on normal voice calls as well.
The ISP's phone company could be having capacity problems, and are unable to connect your call. You'd only see this on calls to your ISP.
The ISP could have a broken modem in their pool. You could try and try and each time reach that same broken modem, until someone else tries, or frees up another working modem, at which point you'd connect. I'd expect your ISP to be on top of this, as I would also expect others to be complaining. But then, not all ISPs are diligent, and as I said, many are starting to devalue their modem pool.
And lastly, it could be your modem. It's possible that your modem has somehow deteriorated and is starting to have problems. The only way I know of to diagnose this specifically would be to try a different modem.
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