RoadRunner SMTP and Mac Mail problem

Hello all. I have set up my new iMac, and am attempting to get my RoadRunner email working. The inbound server (POP) works fine. I can receive email without a hitch. However, the outgoing server is not working, and I get an error message saying that I need to double check the password and username. I have verified with RoadRunner that my server addresses, username, and password are all correct. The RR webmail works fine sending/receiving. The issue seems to be with the Mac Mail program. Any ideas on how I can get it going? I am connected to the internet via my Airport Express wireless network if that matters. (And a RR Cable Modem.) Thank you for any help!

Road Runner SMTP mail is surprisingly difficult to get working with Apple Mail, even if you have all the values exactly correct. I had this issue at a client last week, and these are the instructions I followed to get it working. See the second post in the thread - it does have some confusing steps, so read the following posts too, which clarify them. Basically you're going to set up the account again, manually, but with no SMTP authentication.
http://discussions.apple.com/thread.jspa?messageID=6964913
Hope that helps
Matt

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Many syncing and e-mail problems.

Hi folks, lots of syncing and e-mail problems here:
Syncing: My phone won't sync iCal (it tells me my phone is disconnected), my safari bookmarks or my email accounts. I've been through the threads here, tried resetting iSync, tried deleting calendars and resetting to 10 days instead of 30 -- still no luck. For e-mail, initially iTunes saw the e-mail accounts but did not sync theml. I tried the one-time advance settings and now it's not even seeing the accounts and still not syncing them. and for Safari, no luck with the bookmarks at all even thought the check-box is checked.
Also, the iPhone won't receive e-mail from any of my POP accounts, even the one I set by hand (because none of the settings synced.) I used the same settings that I have on my desktop, but no luck. I use RoadRunner, so I know I can't send off it. But I went to the genius bar today and they told me to just leave the SMTP server field blank and I should be able to receive, but all I get on wi-fi and edge is a message that says, "Cannot Get Mail, the connection to the server "pop-xxxxxx etc" failed." even on my home netowrk, with five bars, it can't seem to connect. (btw, it does seem to be working properly on my .Mac account, but I don't use that account for most of my correspondence.)
As far as the sync problems, the genius bar told me to reinstall iTunes, which I did with the new update that just came out this evening. Still no luck.
any thoughts? bum phone? some setting I'm not catching? any help would be appreciated.
Dave
Quad G5 Mac OS X (10.4.2)

You will find the iPhone will freak out over any kind of perceived data corruption. Calendars seem to the worst for this (windows or mac)
Test in a new user and try sending info in each direction. If it works - then your phone works fine.
Other users have reported having to basically copy the contents of their calendars into a sticky or text edit window. delete the calendars and create brand new ones. they then just transfer the data back.

Does roadrunner work with mac mail??

I linked one roadrunner account to Mac mail but can't get the other one to work (same settings - checked more than once). Anyone else have this problem?

Did you get some kind of Warning like SMTP server already used?
IMHO you would be better off getting Thunderbird as an Email program, Mac Mail Stinks. Just sayin.

G-Mail and Apple Mail problems

I have had tons of problems with my Mail app and Gmail. A window pops open and asks for my password and then does not have any effect on allowing retrieval from the server. Often times I cannot download my mail from gmail at all....have you had similar problems??
OK....
this gmail/mac mail problem caused me a ton of suffering.....but I think I have it figured out....
I think the problem stems from the fact that if you use gmail through a browser and send messages, for example if you are away from your computer, then those sent messages eventually get stored as new conversations. When you return to using your mail app the messages you sent will appear in your inbox as new mail, sent by you.
I am not quite sure how the next step happens but after a lot of fidgeting what I found was that, after erasing my inbox in gmail(this is probably not necessary), after backing up the messages, I went into gmail's preferences and in POP and Forwarding I selected allow POP for all mail. What happened next was unusual....even though the entire mail box on the gmail server was empty.....when Mail started to get the messages it showed that there were over 300 messages to download. The interesting thing was that most of these messages were sent by me to someone else and had an attachment.
After downloading and erasing all these old messages that were causing this case of Mail constipation I went into Mail preferences>>>accounts>>>advanced and clicked the box "remove copy from server after retrieving message" option and then "right away"in the pull down menu. I also clicked the "remove now" button to clear all previously downloaded messages from the server. I noticed on the Mail app that this happened almost immediatly as Mail went about removing all these old messages from the server.
Since this I have not had any problems. I believe that the problem lies somwhere in the way that Gmail creates "conversations". Somehow sent mail gets spirited away in some nook on the server and accumulates, eventually causing a case of constipation. These backed up messages somehow cause the Mail app to not be able to retrieve new messages. If you find this happening do as I have and see what effect it has. Allow your Mail app to down load all the messages it "sees" and keep an eye on what they are(this may take several hours). Often they will be old and previously sent/downloaded mail. Erase them and make sure that they are erased from the server using the advanced option in Mail preferences.
Maybe someone with a more technical background can explain this phenomenon better.
Good Luck.

"A search for Mail AND Gmail in these forums (or a
search for just Gmail restricted to this particular
forum) could have saved you a lot of time and would
have provided you a better understanding of what's
going on (note, it should be "Gmail", not "G-Mail")"
I wonder what the purpose of this reply of yours could be. If it is that something I've said has upset you, I don't know what it could be and I really wouldn't care if it wasn't because your statements could mislead other users into misunderstanding how Gmail actually works. There is nothing in the post that originated this thread that has not already been discussed recently in this forum, except for false assumptions that I'll have to clarify now.
First, choosing a setting in Preferences... > Accounts > Advanced > Remove copy from server after retrieving message has no effect on a Gmail account, absolutely none, no matter whether you choose "Right away", or "After a month" or anything else. Yes, Mail will no longer see those messages, but neither would it had you chosen to leave the messages on the server instead. The messages are simply no longer available there for any POP mail client after having downloaded them. The messages are still on the server, however, and you can read them with a web browser. That's how Gmail works.
Second, clicking Remove now in that same preference pane in Mail has no effect on a Gmail account either, absolutely none. The reason this doesn't work is the same as before. The messages on the server have been hidden by Gmail after downloading them and POP mail clients can no longer see them, nor delete them, nor do anything with them, until you go to the Gmail web site and configure your mail account to make all messages still there available for POP download again.
Third, the only way to get a message deleted from the server with a Gmail account is to log into your account with a web browser. Now, if you want your messages to be deleted immediately after being downloaded by Mail, you can accomplish that by choosing the appropriate setting in the web account settings page -- and you are limited to the options provided there. Mail's own settings will continue to be completely and utterly ignored by Gmail.
Now, had you searched these forums as I suggested or just followed the links I provided in my first reply would certainly have saved both you and me and probably anybody else that chose to read this thread a lot of time.
iMac G5 17" (iSight) Mac OS X (10.4.4)

Outlook and mac mail client attachements freeze, skype freeze

Hi all,
I am working in a company that many users have Macbooks Air and Pro. One specific user with a a Macbook air that has a clean install of Yosemite (not even a week ) started to have problems with the mac mail client attachements. Every time he tried to insert a file the mail client frozen and had to force quit. After a while i observe the same issue on Outlook mail client. At last after a reboot that he did to see if that gonna solve the problem then Skype started to freeze also and had to quit every time. So now, so far none of the above apps work as expected and the Skype doesn't work at all. It has to be noted here that we did the upgrade from Mavericks to Yosemite to solve the Skype issue that he had also for a couple months now and it wasn't resolved from Skype's support team( never answered). So for now we have again the same problem and and with a fresh install of Yosemite i am started to thinking about hardware issues or even broken drivers, code to Yosemite etc. The laptop has an encrypted SSD using Filevault, SEP, Office and Acrobat Reader nothing else.
Any thoughts to solve this issue?

Hi Brody,
Thank you for your answer, yes i did erase the hard drive and install Yosemite!! After a second call that i made with my client he said that first of all:
The problems of the Outlook and mac mail client attachements freeze started after he install Cisco VPN Anyconnect (I don't think that this has to do anything with the freezing) so he tried to remove this using Appcleaner. After this not only the Outlook and mac mail client attachements freeze problem was remaining but he saw that skype started to freeze also. No matter how many uninstall and install he made to the Skype, Skype continues to freeze. For the mail freeze i advise him to use the verify/repair disk permissions and so far that one solved. The remaining problem is the Skype Freeze so far. I also tried to remove the Skype following this https://support.skype.com/en/faq/FA12073/how-can-i-completely-uninstall-and-then -reinstall-skype-for-mac-os-x
so to avoid Appcleaner and still the problem persist even with older versions of Skype. I also create another profile account in Yosemite and Skype seemed to played well there. But i would need to solve in his account so to avoid any file transfer. Do you have any idea why that happened? Is it a file permissions problem? Corrupt/missing files in users profile? This one problem had in the past as i wrote in the previous comment and couldn't work at that time.
Any thought on that? What could be wrong?
Thanks

Downloading of emails via webmail, iPhone and Mac Mail

I currently access emails from my ISP via three avenues. I use webmail when I'm in the office, iPhone on the go and Mac Mail at home. However, I will end up seeing the same emails three times. Even after deleting unwanted emails from my webmail, they will still appear in iPhone and Mac Mail when I access emails and vice versa. Has this anything to do with the POP or IMAP settings? I have set my ISP email on iPhone and Mac Mail under POP. I have ever tried to change the POP to IMAP with same results.
Any advice? Thanks.

I am having the same issue.

My Safari, Address Book and Mac Mail have stopped working.

Recently my Safari, Address book and Mac Mail have become unstable, I cannot edit or copy anything from my Address book, most of the time it'll stop responding before I can even view an address. My Safari keeps freezing and then crashing and I have to force quit, sometimes several times before it'll close. The Mac Mail won't do anything, it tries to download mail and then will sit there doing nothing, again sometimes I have to force quit several times before it'll actually quit.
I have run the extended hardware test and all is fine, I have reinstalled my OS and then restored my info from a backup and still it doesn't work. Can anyone shed any light on this?

Hi jen_bob,
My iMac is a trooper, so far this is the first time its played up - I have I pushed it too far?
I think you've just installed the wrong version of Safari, that's all. Safari 3.x is supposed to be for OS X 10.4 or 10.5 - according to your tag line you are using 10.3.9.
Assuming you are using 10.3.9, then the Safari install will have updated a few system frameworks that are used by other applications (such as Mail). In that case, the 'easiest' way to get things working again is to do an 'Archive & Install' and choose to preserve users and network settings.
http://support.apple.com/kb/HT1710

Problems with authenticated smtp on Mac mail 2

I do support for a small ISP and we are seeing problems with Mac Mail authenticating to the smtp server. The settings that should work are:
outgoing server: asmtp.gorge.net
Username: full email address
Outgoing server port: 2525 or 587
We typically turn on password for the authentication type. In some customers, nothing seems to work. They get an error that their email address can't authenticate. Any ideas on what settings might work for this?

Teri,
Reading the guidance for Outlook Express, I note:
"Step 11. On the Servers tab under Outgoing Mail Server, check the box titled My server requires authentication. Then go to the Advanced tab. Below select the option use same settings as incoming server. (emphasis added)"
In Mail, this is normally the same as specifying authentication of None, and not entering the Username or Password again for the Outgoing Server. This type of authentication, does not result in appending the Username entry (Username corresponds to Account Name in Outlook Express). Mail will authenticate to the SMTP with the Username and Password used for the Incoming, if prompted by the server, and the separate, hard, (and redundant) authentication resulting from using Password in the Outgoing Server entry boxes will cause a failure. However, this type of authentication (which is often called SMTP after POP3, or POP3 before SMTP) is normally conducted on Port 25. In my experience, the use of Port 587 is meant for those SMTP that must have a separate authentication, and where you will see the name altered to include the Username. Hopefully this will work with Port 2525, but I have not confirmed. SMTP after POP3 authentication does not help sending from remote providers, such as found in internet cafes, and this is why some ISPs provide a SMTP that does require separate, Password Authentication.
In the new Mail Setup Assistant, there is now the option to specify to use the same settings, but not enter the Username and Password -- this is not obvious, but well known by some ISPs, but not all -- this is really the same as changing to None in an existing account, and removing the Password and Username entries. Also, in Mail, I would NOT expect any default names to appear, unlike what your Mac Mail instructions imply.
Keep me posted.
Ernie

Mac mail problem with gmail smtp server

I had 2 gmail addresses.
about 3 weeks ago mac mail decided to always send email from both addresses as if they originated from only one address.
I did not solve this problem.
For non related reasons, I got another gmail address.
The same thing started happening.
I now had 3 gmail addresses, but recipients were receiving all email from only one address.
I went to email preferences and started exploring and experimenting.
I was able to reconfigure so that the new gmail address sends from its proper smtp address.
However, there is nothing I can do to get my second email address to send from its proper smtp.
For some inexplicable reason the dialogue box beside "Outgoing Mail Serve (SMTP): tells me that smpt server is offline.
I have no idea how to get it back online.
(In the server editor, there is one more gmail smtp server than I need, 4 instead of 3 and 2 are offline - one just went off tonight)
All relevant mail boxes are online.
Does anyone know anything about this problem?

Jack,
There are mail forums in the forums for OS X, because you are using Leopard 10.5.6 (why haven't you upgraded to 10.5.8?) you should re-post in that forum. Mail comes as part of the OS that is why they're there. The address is:
http://discussions.apple.com/forum.jspa?forumID=1223
Regards,
Roger

Problem with exchange 2007 SP3 and mac mail app loading mails

Hi,
since a few days i am having a problem with mac's (using either the included mail app or outlooc 2011 for mac) syncing mails with my exchange server. both, mail and outlook) connect successfully to my excahnge 2007 sp3 rollup 14 server, but when
they start syncing mail they dont load any mails or only load the headers and keep saying loading (of body)
when i open the https://server/EWS/Exchange.asmx on the browser it asks for the user/pwd and lets me open the xml once, the next time it crashes.
in the eventlog i am getting the error that: a process for app-pool MSExchangeServicesAppPool couldnt respond to a ping. the event id is 5010.
all my microsoft outlook accounts, outlook web acces and the mail on mobile devices (iphone and android) work fine.
does anyone have an idea what could be the issue for this strange behavior?
thanks,
chris

Hi,
According to the error message, "a process for app-pool MSExchangeServicesAppPool couldnt respond to a ping. the event id is 5010", I find a related article for your reference:
Event ID 5010 — IIS Application Pool Availability
http://technet.microsoft.com/en-us/library/cc734991(v=WS.10).aspx
Please follow the article to check whether application pool has been started.
Additionally, I notice that you said "all my microsoft outlook accounts, outlook web acces and the mail on mobile devices (iphone and android) work fine.", please run following command to check whether parameter "EwsAllowMacOutlook"
value is True:
Get-CasMailbox | FL
If the parameter "EwsAllowMacOutlook" value is False, please set it to True via following command:
Set-CasMailbox -Identity FQDN -EwsAllowMacOutlook $True
If still not work, please contact MAC Support for help. For your convenience:
http://answers.microsoft.com/en-us/mac/forum/macoutlook?tab=Threads
Thanks
Mavis Huang
TechNet Community Support

Problem with Blueyonder servers and Mac Mail

I have experienced considerable difficulty in setting up my Blueyonder email account on my new MacBook Air running Mac Mail in Yosemite. After spending over eleven hours with very helpful second line technical support staff at Apple and Virgin Media (both companies wouldn't accept responsibility for the problem unsurprisingly!) I have been forced to the conclusion that I simply can't use Mac Mail and my Blueyonder account.
The problem was fixed by ditching Mac Mail in favour of a new Mail Client as the prospect of changing my email account (with all the consequent notifications to people/organisations set up to use my Blueyonder address) was too depressing!
I firstly used 'Inky' which is free and really easy to set up as it finds the servers and ports for you and (only because I didn't like Inky's layout) I bought 'Postbox' (available on a 30 day free trial) which looks almost identical to Mac Mail, finds the servers and ports for you and has a number of really useful additional features that I'm currently exploring.
Has anybody else experienced this incompatibility problem and, if so, was there a fix I missed?

I have the same problem, basically Mail sometimes works but then will stop and the only way to get it working again is to completely delete the mail account (off the mac) and start again.
Almost at the point now of trying a new mail client as this is really annoying!

Unable to access webmail in browser and Mac Mail

I am a Mac convert from PC and I love my Macbook Pro with Retina display that came with Mountal Lion. Until recently after my visit overseas, I am neither able to access my ISPs webmail through Safari or Firefox on my laptop nor through Mac Mail app with unchanged settings provided by Road Runner, such as webmail.kc.rr.com, apop-server.kc.rr.com/smtp-server.kc.rr.com/110/25. Safari is too slow and hangs with connection errors for webmail. My ISPs id is my business id I use as I travel overseas constantly. I spent several hours and had my spouse call in local tech support and it is a pain having to call your spouse to login and forward email to a public email. Any help is appreciated as my ISP has been anything but helpful in resolving this issue blaming the OS.

Thanks for your reply, Sig. I spent over three hours with my ISPs support tech, deleted and added my account, and even rebuild was of no avail. From Terminal, I am able to ping and I get an IP address but when I try connecting to webmail server, the browser returns an connection error, in Mac Mail I get the following message,
"Unable to receive Mail -
There may be a problem with the mail server or network. Verify the settings for account “Road Runner” or try again.
The server returned the error: The connection to the server “pop-server.kc.rr.com” on port 110 timed out." The tech asked me to check with the local ISP who directed me to ask Road Runner to clear the block off SMTP port.
I have not used mail2web until now, but would give it a try if it resolves my issue. Thanks for your help and assistance.

SMTP on Mac Mail all Stopped Working

Hi, back already! Well everything was going great until I tried to send an email with mac mail. All my SMTP services are not resolving. One outlook one and two from my own website email.
Applied a fix that I found on the apple forum but wondered if this was an "approved" fix. I mean it works but is this the best way to deal with it? I changed my DNS server to 208.67.222.222 and they resolved. Is that the best way to deal with this?
Thanks!
Solved!
Go to Solution.

Before I changed the DNS server I tried relaunching mac mail, rebooting the computer & restarting the router to get a new IP (I wondered if I'd been allocated an IP address that had previously been used for spam) None of these worked.
Both the OpenDNS and GoogleDNS both resolved the problem. To clarify it was two email accounts hosted by heart internet (smtp.outitgoes.com) and one outlook.com (smtp.live.com) perhaps these SMTP servers need to be added to a "safelist" within BT systems, I dunno. I've switched to GoogleDNS so I'll just leave it at that, no issues there so that's fine.

SMTP POP Mac mail Yosemite Upgrade Issues

I have used mac mail for years with little or no problem, however, Yosemite is another story.
The SMTP outgoing mail will not work.
Often times when I am trying to figure out the problem by input changes into my mail preferences
the computer does not ask me to save. Thus it all goes back offline. The problem just all of a
sudden happened with no reason and for a week now, off and on I have been trying to fix this.
Apple charges money over the phone, have to drive 30 miles to a genius bar or fix it myself.
Should I try to go backwards to Maverick? My Yosemite upgrade originated from Snow Leopard.
I thought Apple was the computer elite. What was wrong with the old email? I'm so frustrated.

Open Mail app, go to the top panel and select WIndow > Connection Doctor.
What is the error message (or messages) that the Connection Doctor is reporting?
How to troubleshoot mail issues: OS X Mail: Troubleshooting sending and receiving email messages - Apple Support
Who is your email provider (for privacy reasons please DO NOT provide your full email) and do you have correct settings?
https://www.apple.com/support/mail-settings-lookup/

Smtp-server (outgoing mail) problem on MAIL

Time Warner/road runner technician cannot figure out m youtgoing (smtp) email connection. No way of authenticating the smtp-server.nyc.rr.com. The Apple=software on my new Mac mini is too advanced for TW help site. They told me to solve "smtp-server problem" though MAC mini help site.
How can I get the smtp server to work so that I can send out my emails on my mac-MAIL program
Irene Schmied

what is the smtp server info they have told you to use?
in Mail>preferences>accounts, make sure your TW account is selected in the left hand side of the window, then go to the Account Information tab, then go to the Outgoing Mail Server (SMTP) option at the bottom of that window, click on it, and go to Edit Server List, what is showing as server name? an if you click on Advanced, what is the server port, is SSL checked, and is authentication set to password, and if so do you have the user name and password entered?
let me know

RoadRunner SMTP and Mac Mail problem

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