SSL for outgoing mail via iCloud

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SSL for outgoing mail via iCloud

Post by Malbone on Mon Dec 19, 2016 4:43 pm

I am in the slow process of switching from Eudora to Pandora, but I have hit a snag.  I can receive email on my iCloud account via Pandora, but cannot send it.

The log displays the error message:

Task: Sending 'test from icloud-pandora' [<Dominant>]
Status: Not Completed
Details: Connection with mail server [redacted to avoid having it look like an "external link"] was not established. Error #: 10060
Completed: 3 %
Time: 12/19/2016 11:22:58 AM

I am using the settings  recommended by Apple, which I have used in Eudora without any problem:

   SSL Required: Yes
   If you see an error message when using SSL, try using TLS or STARTTLS instead.
   Port: 587
   SMTP Authentication Required: Yes
   Username: Your full iCloud email address
   Password: Your iCloud password

The only thing I can think of is that perhaps Pandora uses a different SSL implementation than Eudora, and does not offer a way to change that.  Is there an .ini file or other hidden setting that I can change manually?  Without a manual, it's hard to find this stuff by trial and error.

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Re: SSL for outgoing mail via iCloud

Post by Admin on Mon Dec 19, 2016 8:28 pm

Hello Malbone, and welcome to Pandora Forum.

We had exactly the same case last week, and the week before.
EDIT: iCloud SMPT proxy server that supports STARTTLS but does not support SSL/TLS.

TLS and STARTTLS are not synonymous, while practically SSL and TLS are. So:
1. Plain Text - Supported
2. SSL/TLS - Supported (That's a real deal encryption)
3. STARTTLS - Not supported (STARTTLS is misleading at best. It's really plain text, negotiation plain text and after it - maybe TLS. Few early versions supported it - however many servers would negotiate negative while if you start SSL/TLS from the get go - working wonderfully.)

So if it's 1. or 2. just check:
Authentication: CRAM-MD5
and of course:
For Plain Text -> Secure Sockets -> Never
For SSL/TLS -> Secure Sockets -> Always

If their CSR tell you they support secured connections and it's STARTTLS, tell them that's not secured and if they can implement the real deal - SSL/TLS. They can do it in a day.


Last edited by Admin on Mon Dec 19, 2016 11:32 pm; edited 1 time in total
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Re: SSL for outgoing mail via iCloud

Post by Malbone on Mon Dec 19, 2016 10:55 pm

Apple says ( support.apple.com/en-us/HT202304 ) that these are the IMAP connections they support:

IMAP information for the incoming mail server

   Server name: imap.mail.me.com
   SSL Required: Yes
   If you see an error message when using SSL, try using TLS instead.
   Port: 993
   Username: This is usually the name part of your iCloud email address. If your email client can't connect to iCloud using just the name part of your iCloud email address, try using the full address.
   Password: Your iCloud password

SMTP information for the outgoing mail server

   Server name: smtp.mail.me.com
   SSL Required: Yes
   If you see an error message when using SSL, try using TLS or STARTTLS instead.
   Port: 587
   SMTP Authentication Required: Yes
   Username: Your full iCloud email address
   Password: Your iCloud password


I am having trouble sending mail via Pandora when Eudora (on the same machine) works just fine.

For outgoing mail, there are 3 independent variables:

1.  Authentication: Basic or CRAM-MD5
2.  SSL: Always or Never
3.  Use submission port (587) or not (SMTP Port 25 or 465, depending on SSL setting)

That produces 8 possible permutations.  I tried all 8.  None of them worked.

For incoming mail, the IMAP settings work fine under Pandora (Basic authentication; SSL Always; IMAP Port 993).  So as far as I can tell there isn't a password, firewall, or other connection issue.

What more could be going on?

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Re: SSL for outgoing mail via iCloud

Post by Admin on Mon Dec 19, 2016 11:48 pm

so their SMTP server fully supports SSL/TLS (not just STARTTLS)

> SMTP Authentication Required: Yes

do you know exactly what kind of authentication. is it CRAM-MD5, or some other flavor?
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Re: SSL for outgoing mail via iCloud

Post by Malbone on Tue Dec 20, 2016 4:12 am

I don't have access to Apple's developer site, but some general internet searching leads me to suspect authentication is plain text.  See the example at:

www dot jqueryform dot com/help/icloud-smtp.php

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Re: SSL for outgoing mail via iCloud

Post by Admin on Tue Dec 20, 2016 2:09 pm

that's STARTTLS allright, and authentication is plain.

was it a good guess or what, you are allowed to say "you've been reading my mail", all pun intended.

if you want advise: get a SMTP server with a proper TLS/SSL support (required; ask them specifically: is it STARTTLS extension or fully fledged SSL/TLS).
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Re: SSL for outgoing mail via iCloud

Post by Malbone on Tue Dec 20, 2016 10:30 pm

Well, Apple is out, and Yahoo is also out because it, too, only uses STARTTLS to send. I may have to use Gmail, which I have been trying to avoid for privacy reasons (ironic, then, that Gmail does use SSL/TLS).

Since you support full SSL and you also support non-SSL password authentication, why don't you support STARTTLS? I ask as someone who knows nothing about the programming difficulties involved.

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Re: SSL for outgoing mail via iCloud

Post by Admin on Wed Dec 21, 2016 6:09 am

No it doesn't - Yahoo supports SSL/TSL. Most servers switched to SSL/TLS by now, in fact these 3 iCloud/SMTP cases (could as well be the same server) were the first one reported using exclusively STARTTLS.

Look no further than this thread: you thought it was secure (and so did many other), their web site told you it was secure.. just misleading, obsolete extension. Avoid.
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