I have about 12 gmail addressees running though my Mail application, 1 Mac address @me.com and one Rogers address.
I was using one software I loved called MAILPLANE that dealt extremely well with Gmails so I had at one point, both email programs handling all my mail but since I upgraded to the latest OSX the MAILPLANE that works with it, is newly designed and I dont like it.
So I am back temporarily to running it all through MAIL but am encountering the same problems I have had for years when dealing with multiple addressees in any email program whether it was Mac or Windows based software.
I find that the mail will work great for several days but then slowly one email addresses box will pop up and I will have to fill in its password, over and over even though I am doing the right one.
That might settle down after a day or two BUT IF i ever have more than one @me.com or more than one @icloud.com address, as well as more than one @rogers.com, my main ISPs email, they will never seem to allow more than one. Forget trying to collect email for two different @me.com addresses yet i have no idea why this is so?
I can be fine for days or even weeks but now, just like today, out of all my addresses, it will show about 5 servers offline. I can keep pressing something to put them online with Gmail but they will all pop offline again...... When I go into the settings, I will see that the password area that was fine earlier is now blank or the outgoing mail server will suddenly show itself as offline on a couple of them and the little box below you check off that says USE ONLY THIS SERVER will become unchecked and until I manually recheck it and point it towards the right server i will have problems with that account.
I have 2 macbooks set up right now with half on one and half on another and i am sliding back and forth between the two and its just not working well ;-(
I am stuck as to what to do.
Do I somehow limit my email addresses to half of what I have, somehow?
Do i forward some to one address and then somehow set it up so the person I email will reply to the original address that will then forward to the one i set it up to rather than the forwarded address......or what?
I cant think anymore as to how to solve this dilemma.
Is there some sort of rule whereby you can only use so many email addresses and if so, why does it work perfectly at one point but then other times several are wonky at once?
Does anyone have any ideas of how to deal with this ongoing problem???

I cant be the only person with so many email addresses but while at it, does anyone know WHY I am unable to use 2 @me.com addresses in one email or the same with Rogers addresses as I cant use two either in one program?
I have tried asking Rogers this over the yeas but never once got a reasonable answer.
Thank you!!! ;-)
I was using one software I loved called MAILPLANE that dealt extremely well with Gmails so I had at one point, both email programs handling all my mail but since I upgraded to the latest OSX the MAILPLANE that works with it, is newly designed and I dont like it.
So I am back temporarily to running it all through MAIL but am encountering the same problems I have had for years when dealing with multiple addressees in any email program whether it was Mac or Windows based software.
I find that the mail will work great for several days but then slowly one email addresses box will pop up and I will have to fill in its password, over and over even though I am doing the right one.
That might settle down after a day or two BUT IF i ever have more than one @me.com or more than one @icloud.com address, as well as more than one @rogers.com, my main ISPs email, they will never seem to allow more than one. Forget trying to collect email for two different @me.com addresses yet i have no idea why this is so?
I can be fine for days or even weeks but now, just like today, out of all my addresses, it will show about 5 servers offline. I can keep pressing something to put them online with Gmail but they will all pop offline again...... When I go into the settings, I will see that the password area that was fine earlier is now blank or the outgoing mail server will suddenly show itself as offline on a couple of them and the little box below you check off that says USE ONLY THIS SERVER will become unchecked and until I manually recheck it and point it towards the right server i will have problems with that account.
I have 2 macbooks set up right now with half on one and half on another and i am sliding back and forth between the two and its just not working well ;-(
I am stuck as to what to do.
Do I somehow limit my email addresses to half of what I have, somehow?
Do i forward some to one address and then somehow set it up so the person I email will reply to the original address that will then forward to the one i set it up to rather than the forwarded address......or what?
I cant think anymore as to how to solve this dilemma.
Is there some sort of rule whereby you can only use so many email addresses and if so, why does it work perfectly at one point but then other times several are wonky at once?
Does anyone have any ideas of how to deal with this ongoing problem???
I cant be the only person with so many email addresses but while at it, does anyone know WHY I am unable to use 2 @me.com addresses in one email or the same with Rogers addresses as I cant use two either in one program?
I have tried asking Rogers this over the yeas but never once got a reasonable answer.
Thank you!!! ;-)