Problems setting up 2nd email address

Ok so I followed all the help instructions for setting up a second email address and all is fine. I can send test emails to my first account and I receive them within the same inbox. But then I hit two roadblocks:
1.) When I reply to the test message it bounces back.
" (reason: 550 5.1.1 unknown or illegal alias"
2.) The password window keeps popping up. After entering my password I get "The POP server “pop-server.nyc.rr.com” rejected the password for user “(my new email account)”
What's going on???

These 4 email accounts are provided by who?
Your internet service provider or an email account only provider or a combination?
Any error message provided when the Mail.app checks these accounts for new messages and the same when attempting to send?
Port 587 is used for an SMTP server port which has nothing to do with receiving messages.

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I have just had an IT professional overhaul my business email and (I think) I have new settings however I found all relevant details but cannot reconnect my business email to my phone. My personal email is on there fine
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It can take 15-20 mins for the BIS to start pushing the emails to your device.
Also, make sure you in Outlook Express you have it set to "leave messages on server". I don't know exactly where that option is in Outlook Express, but it will be similar to that in Outlook:
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There is a setting in Outlook to "Leave Messages on Server".
For MS Outlook 2003:
1. Outlook > Tools > Email accounts > View or Change existing > next.
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You must be talking about email aliases. Log into icloud.com with a browser, go to the email page and click the cog wheel icon in the upper right. Go to preferences>accounts. YOu can define aliases there. Note that they must now be @icloud.com named emails.

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Using Mail in Mac OS X 10.6.2 and moving to Mac for the first time, I have been unable to set up two email addresses on the same account. Entering them, separated by commas, as advised in the Help does not seem to work. I have tried making them both the same password and have tried separating the passwords with a comma but no luck. Unable to set up another account for the second address because it correctly tells me that the account already exists.
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After a comprehensive trial and error session, using a new Guest Account each time to be sure of no contamination from the previous trial, I have finally cracked it!
The problem was logging on to the outgoing server.
Setting up the first account was fairly straightforward but if I allow Mail to do it automatically I am unable to send because Mail has defaulted to 'Authentication Required' when my server does not require it. Setting the account manually without authentication enables send and receive to work OK.
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I eventually found that if I uncheck the 'Always Use This Server' box, all account then use the server on the first account, which is correctly set up.
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Problems setting up 2nd email address

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