Does anyone use a Mac? Problems sending email

[minskey]

My Oh is at his witts end as he cannot send emails............

He is fine receiving, it won't send. Checked all the ports ets and obvious places. Been on the Apple website and also contacted our ISP, no joy there.

He had a trial of Outlook for mac which worked perfectly. Mac mail was working but died on the 8th of Jan.......................... help its driving us nuts

[chris]

Are they just in the outbox? Are you using Mail.app (the default mail client in OS X)?

I'd hazzard a guess and say that it's your SMTP (send mail) server settings. Who is your ISP? What domain does your email address end in? (like mine is @gmail.com).

[minskey]

Hi Chris
Yes just outgoing mail,
Yes using Mail.pp
ISP is 'Easily' SMTP is smtp.easily.co.uk

[VirginVegGrower]

Is it full!? A large file blocking all others? Look at your folders and maybe do some clearing. Although it would warn you.
Mail server setting for sending are incorrect as Chris says above would be my guess.

[chris]

Hi Chris
Yes just outgoing mail,
Yes using Mail.pp
ISP is 'Easily' SMTP is smtp.easily.co.uk

Can't see anything on their site, but perhaps they need authenticated smtp? - enter your ISP/Email username/password in Mail -> Preferences -> SMTP server (open the drop down list, and select edit), click advanced, in the authentication dropdown list - choose password, then enter your credentials there. If that doesn't work, what is the error message?

[minskey]

Virginveggrower; no not full.

Chris; tried that, its so frustrating.

I'm still waiting to hear back from Easily.

This is the error message; could not connect to this smtp server.

Just read the error report and it says; EHLO unknown and lots of other computer speak, another one says '501 syntactically invalid EHLO argument'

[chris]

What port is configured? 25?

Could
You post the whole log from start of the connection? The EHLO is like "hello" when a connection is made.

[minskey]

here goes;

CONNECTED Feb 03 18:31:04.213 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000



READ Feb 03 18:31:04.242 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000
220 smtp2.easily.co.uk ESMTP ready at Sun, 03 Feb 2013 18:31:03 +0000

READ Feb 03 18:31:04.243 [kCFStreamSocketSecurityLevelNone] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0
+OK Welcome to the Easily mailserver.

WROTE Feb 03 18:31:04.256 [kCFStreamSocketSecurityLevelNone] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0 CAPA

WROTE Feb 03 18:31:04.257 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000 EHLO unknown-68:a8:6d:2b:f1:18.home

READ Feb 03 18:31:04.286 [kCFStreamSocketSecurityLevelNone] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0
+OK
CAPA
TOP
UIDL
RESP-CODES
PIPELINING
STLS
USER
SASL PLAIN LOGIN DIGEST-MD5 CRAM-MD5
.

READ Feb 03 18:31:04.291 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000
501 Syntactically invalid EHLO argument(s)

WROTE Feb 03 18:31:04.320 [kCFStreamSocketSecurityLevelNone] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0 STLS

WROTE Feb 03 18:31:04.323 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000 EHLO unknown-68:a8:6d:2b:f1:18.home

READ Feb 03 18:31:04.354 [kCFStreamSocketSecurityLevelNone] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0
+OK Begin TLS negotiation now.

READ Feb 03 18:31:04.358 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000
501 Syntactically invalid EHLO argument(s)

WROTE Feb 03 18:31:04.374 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000 RSET

READ Feb 03 18:31:04.404 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000
250 Reset OK

WROTE Feb 03 18:31:04.408 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000 HELO unknown-68:a8:6d:2b:f1:18.home

READ Feb 03 18:31:04.443 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b54400 -- thread:0x7ff4c2228000
501 Syntactically invalid HELO argument(s)

INITIATING CONNECTION Feb 03 18:31:04.449 -- host:smtp.easily.co.uk -- port:25 -- socket:0x0 -- thread:0x7ff4c2228000

READ Feb 03 18:31:04.478 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:imap.mail.yahoo.com -- port:993 -- socket:0x7ff4c3934e60 -- thread:0x7ff4c235ef00
* OK [CAPABILITY IMAP4rev1 ID NAMESPACE X-ID-ACLID UIDPLUS LITERAL+ CHILDREN XAPPLEPUSHSERVICE XYMHIGHESTMODSEQ AUTH=PLAIN AUTH=LOGIN AUTH=XYMCOOKIE AUTH=XYMECOOKIE AUTH=XYMCOOKIEB64 AUTH=XYMPKI] IMAP4rev1 imapgate-0.7.68_14.357900 imap405.mail.ird.yahoo.com


CONNECTED Feb 03 18:31:04.491 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b8af60 -- thread:0x7ff4c2228000



READ Feb 03 18:31:04.524 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b8af60 -- thread:0x7ff4c2228000
220 smtp3.easily.co.uk ESMTP ready at Sun, 03 Feb 2013 18:31:04 +0000


WROTE Feb 03 18:31:04.541 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b8af60 -- thread:0x7ff4c2228000 HELO unknown-68:a8:6d:2b:f1:18.home


.


WROTE Feb 03 18:31:04.572 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0 AUTH CRAM-MD5

READ Feb 03 18:31:04.573 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b8af60 -- thread:0x7ff4c2228000
501 Syntactically invalid HELO argument(s)


READ Feb 03 18:31:04.606 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0
+ PDc4NDIzODc1NDkxMjM1ODIuMTM1OTkxNjI2NEBzb3VtYWlscHJveHkwMj4=


WROTE Feb 03 18:31:04.615 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b8af60 -- thread:0x7ff4c2228000 HELO unknown-68:a8:6d:2b:f1:18.home


WROTE Feb 03 18:31:04.653 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0 aW5mb0BhcnRvZmNpcmN1cy5jb20gY2QwZWY0OGYyMDk1ZGIwYTBhYTNjMjBjY2E1ZWQ1ZTE=


READ Feb 03 18:31:04.666 [kCFStreamSocketSecurityLevelNone] -- host:smtp.easily.co.uk -- port:25 -- socket:0x7ff4c4b8af60 -- thread:0x7ff4c2228000
501 Syntactically invalid HELO argument(s)


READ Feb 03 18:31:04.701 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0
+OK Logged in.


WROTE Feb 03 18:31:04.756 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0 QUIT


READ Feb 03 18:31:04.797 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:mail.easily.co.uk -- port:110 -- socket:0x7ff4c3deecf0 -- thread:0x7ff4c23ed4c0
+OK Logging out.

[chris]

What are you entering as your username? Sorry about the delay was bathing the kids

Edit: try it without the @easily.co.uk, or with if you don't have it on there. If you have a full stop in the email address make sure it's a full stop and not a comma. The only special characters allowed in an email address are "-", ".", "+" and "_" off the top of my head.

Edit2: is your send mail server set as easily, or your yahoo one? -- when you're sending the email, are you selecting to send from your easily? 99% of ISPs will not allow you to send from another domain via their send mail/relay servers, so if you're set to send via easily, and you're composing from your yahoo that'd cause issues (unless there's a trust between the two)... Probably not related (I'm guessing either a username or password issue - might be worth logging into the web mail, and if that works, copying and pasting the user into the send dialog settings in mail.app).

Failing that, I'd suggest trying another mail client to make sure it's not an issue with mail.app's smtp protocol (though I highly doubt that, as mail clients are made to work with smtp (send mail protocol (protocol being the language, or syntax used to communicate)).

Edit3: Is it a secondary email address setup on your isps mail account? If that is the case, then try using the primary username/password in the send settings. Maybe a screenshot of the dialog (send mail) would be helpful..

Edit4: - final edit!

I'm 99% sure it's a username issue, as the SMTP server is saying it doesn't recognise the HELO and the EHLO command.. HELO is a basic set of instructions, with EHLO being an optional, more advanced set (which I'm guessing is things like sending SSL-based email -- looking at your TLS stuff, I'm guessing you are sending secure emails).

[minskey]

Well, Oh has spent hours on this; nothing is working. Trawed the interweb and there are loads of other people with the same problem, apparently a 'mac' bug!

Given in and downloaded Opera mail client, put his settings in and its working!!!!

I know its very annoying, Macmail should work but it doesn't. I'll have another go when I'm not so desperate for time, keep you posted too.

Many, many thanks for your help one & all