Strange email issue on Macbook air

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Strange email issue on Macbook air

Postposted on Thu Jun 26, 2014 10:59 pm

Let me preface this by saying the last time I used a mac, was back in the PowerPC/OS7 days, and I did graphic design work on them, so obviously I'm pretty much clueless about the advances up to whatever the lastest OSX rev is.

I got volunteered recently to help a friend of a friend with email problems. She can receive. but not send. We verified connectivity,and her passwords, so I started checking out her mail client (I think it's the standard mail icon). When I was checking out her accounts, and the statuses of them (she uses her client for 3 separate email accounts), all the smtp servers (she had 4) were all marked offline. No amount of trying to bring them up did any good, so she can't reply to anybody.

Any ideas on what could've happened, thinks to check out? I spent most of my time with routers, switches, wireless backhauls, and telecommunications equipment, so I am basically a neophyte at this. Any and all help will be appreciated.
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Re: Strange email issue on Macbook air

Postposted on Fri Jun 27, 2014 10:32 am

My wife has about six different email accounts for her jobs, so I have some experience how frustrating this can be.

Off the top of my head, here are a couple ideas.

The SMTP servers might need authentication to be turned on, or they might have some other misconfiguration. Apple Mail hides the SMTP settings in its preferences, so working with the accounts in the Accounts section doesn't help.

The SMTP servers may be rate limited, and your friend's friend could be running into this. There was one particular server that would make my wife wait for five to ten minutes after sending an email before sending another.

Gmail with two-factor authentication has application specific passwords which are separate from the regular Gmail password, and they don't need to be changed.

More information about the servers would be helpful.
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Re: Strange email issue on Macbook air

Postposted on Fri Jun 27, 2014 10:52 am

It's also possible that the ISP has decided to start blocking outbound port 25 (which smtp uses) as an anti spam measure. You can do a very crude test from the terminal on a mac by typing this in:
telnet your.smtp.server.com 25

I don't actually have a mac to try that command on so the syntax might be a little different. Just for reference here's the output I get under linux:
Code: Select all
chrubuntu:~$ telnet smtp.gmail.com 25
Trying 173.194.66.108...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.
220 mx.google.com ESMTP o12sm79189588wiw.5 - gsmtp
^]

telnet> quit

If port 25 is being blocked you'll never get anything beyond the "Trying ..." line.


If port 25 is being blocked you might try port 587 (usually requires TLS security) or port 465 (requires SSL security). Though whether either of these work depends on how the smtp servers are setup.
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Re: Strange email issue on Macbook air

Postposted on Fri Jun 27, 2014 12:58 pm

Flatland_Spider wrote:My wife has about six different email accounts for her jobs, so I have some experience how frustrating this can be.

Off the top of my head, here are a couple ideas.

The SMTP servers might need authentication to be turned on, or they might have some other misconfiguration. Apple Mail hides the SMTP settings in its preferences, so working with the accounts in the Accounts section doesn't help.

The SMTP servers may be rate limited, and your friend's friend could be running into this. There was one particular server that would make my wife wait for five to ten minutes after sending an email before sending another.

Gmail with two-factor authentication has application specific passwords which are separate from the regular Gmail password, and they don't need to be changed.

More information about the servers would be helpful.



She's using AOL as her personal mail account, and she using a regular Gmail account, and one business account that somehow maps to the gmail account. She's a missionary at my mom's church, so I'm kinda loathe to name the organization.

And you're right, it wasn't in the account tab, it was one of the other tabs (Open Mail, click the Mail option at the top left, and it was one of those options). In one of those, it showed 4 smtp servers (Gmail, AOL, smtp.gmail.com, and smtp.aol.com) as all being "offline". There was an option to "take all accounts online", but it did nothing. We verified her passwords, and all the various SMTP acct options (port number, require SSL, etc...)

I ended up passing the buck off to her IT at the missionary group, since I have very little experience with Macs (I've used Amigas and Apple IIe's more than I have modern Macs). I was just curious, since I may run into the issue again with other folks. My mom has a terrible habit of trying to make me the volunteer IT guy for her church friends...

Lastly, one of my first jobs in IT was as admin for Exchange 5.5, and whatever mail server that Sun box ran, AND I HATED EVERY SECOND OF IT. I'd rather be stuck in the hot sun repairing fiber bundle cuts, or standing on top of a watertower, trying to aim a parabolic dish at it's mate 5 miles away using nothing but binoculars and a multimeter.
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Re: Strange email issue on Macbook air

Postposted on Fri Jun 27, 2014 7:27 pm

cheesyking wrote:It's also possible that the ISP has decided to start blocking outbound port 25 (which smtp uses) as an anti spam measure. You can do a very crude test from the terminal on a mac by typing this in:
telnet your.smtp.server.com 25

I don't actually have a mac to try that command on so the syntax might be a little different. Just for reference here's the output I get under linux:
Code: Select all
chrubuntu:~$ telnet smtp.gmail.com 25
Trying 173.194.66.108...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.
220 mx.google.com ESMTP o12sm79189588wiw.5 - gsmtp
^]

telnet> quit

If port 25 is being blocked you'll never get anything beyond the "Trying ..." line.

If port 25 is being blocked you might try port 587 (usually requires TLS security) or port 465 (requires SSL security). Though whether either of these work depends on how the smtp servers are setup.




I forgot to reply to this earlier (sorry!), but I checked the port settings, and none were on default ports. They were setup for the specific ports Gmail and AOL used. Basically her mail went from working to not working overnight, and I didn't change any settings beyond having her re-enter her passwords, and trying to force the 4 smtp accounts to go online. I asked if she made any changes, but she didn't recall, so I had no qualms of punting this off to someone else. :P
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Re: Strange email issue on Macbook air

Postposted on Fri Jun 27, 2014 7:35 pm

I'd tell her to stick to the gmail web interface and set gmail up to download the AOL accounts, minimum work for you :wink:
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Re: Strange email issue on Macbook air

Postposted on Fri Jun 27, 2014 7:43 pm

cheesyking wrote:I'd tell her to stick to the gmail web interface and set gmail up to download the AOL accounts, minimum work for you :wink:



Nah, it's just a friend of my mom's from her church. Once I saw it was a Mac book, I warned her that I may not be able to fix it. I'm just curious as to why those "(offline)" messages showed up.

If you have a mac handy, open up Mail, and then click Mail in the upper left corner. It might be preferences, or something I clicked, but it opened a box that listed her 3 email accounts:

Gmail
AOL
[redacted]

When you selected one of those, it showed connection information on the right (SSL, port number, server name, user/pwd, etc..), and for all three of those accounts, she had 4 (?!) smtp options:

Gmail (offline)
AOL (offline)
smtp.gmail.com (offline)
smtp.aol.com (offline)

No amount of choosing "force online" (or whatever that options was) did anything. I verified she had full internet connectivity. I'm just curious what the deal was, since I don't like not being able to fix things. I'm just super-nerdy like that. :)



*EDIT*

It just dawned on me I have (had?) a custom copy of OSX Snow Leopard for VMWare somewhere. I wonder how I can replicate the problem, to see if I can fix it?

/White & Nerdy
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Re: Strange email issue on Macbook air

Postposted on Sat Jun 28, 2014 3:14 pm

The thing is email works the same on pretty much every operating system. It's not really an OS X problem as much as it's a configuration or network problem. IMAP, POP, SMTP, and MAPI are all supported by Apple Mail.

Opening Connectivity Doctor (Window > Connectivity Doctor) will give you some good diagnostic information.

It's Mail > Preferences > Accounts then Advanced and selecting Edit SMTP server list from the SMTP server drop down menu to edit the SMTP server properties.
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