SSL IMAP Errors - iOS 17

Problem reported by Chris Danks - 6/8/2023 at 3:41 AM

Not A Problem

since I upgraded my iPhone to iOS 17 I get this error when connecting to IMAP SSL:

We're on build:

SmarterMail Enterprise

Build 8451 (Feb 20, 2023)

I'll try upgrading to the new build later tonight to see if it fixes it, but wondering has anyone else seen this and know if its fixed in a newer build of smartermail?

23 Replies

Reply to Thread

Kyle Kerst Replied

6/8/2023 at 7:51 AM

Employee Post

I know the newest iOS versions are increasingly intolerant to security issues (certificate name mismatches and such) so you might want to double-check those areas in addition to the update. iOS also does email privacy things now where it will hide your IP and disguise other details about you and your device - so you could try turning these off temporarily to see if it helps as well. I hope that helps!

Kyle Kerst IT Coordinator SmarterTools Inc. www.smartertools.com

Kyle Kerst Replied

6/8/2023 at 7:53 AM

Employee Post

Also, after responding to you I noticed the POSIX 57 error and did a little bit of reading. It sounds like that error indicates the Apple Mail code detected a lack of network connectivity to that host:

https://developer.apple.com/forums/thread/67606

So I'd be on the lookout for hostname or security settings issues, something preventing your device from reaching the server. If you need a hand please submit a ticket and we'd be happy to help dig into it!

Kyle Kerst IT Coordinator SmarterTools Inc. www.smartertools.com

Chris Danks Replied

6/8/2023 at 12:28 PM

Hey

I upgraded tonight to:

SmarterMail Enterprise

Build 8552 (Jun 1, 2023)

The issue continued, I then found this option in settings > Mail on my iPhone:

it was turned on:

I turned it off:

I then turned OFF my iPhone and back on

After a few minutes I again tried to access my email and its just stuck on connecting.

I can connect fine via AciveSync to another account on the same SM its just IMAP.

I tried turning OFF SSL too on the IMAP settings so it uses port 143 however the issue remains.

Chris Danks Replied

6/8/2023 at 12:30 PM

to add to this my IMAP log on the server looks unusual!

[2023.06.08] 20:18:28.450 [IP Unknown][64251036] Authentication failed because the remote party has closed the transport stream.
[2023.06.08] 20:18:31.489 [IP Unknown][2460242] Authentication failed because the remote party has closed the transport stream.
[2023.06.08] 20:18:45.874 [IP Unknown][64827819] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:18:45.874 [IP Unknown][64827819] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:18:47.544 [IP Unknown][478762] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:18:47.544 [IP Unknown][478762] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:19:58.075 [IP Unknown][2341498] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:19:58.075 [IP Unknown][2341498] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:20:02.780 [IP Unknown][14885832] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:20:02.780 [IP Unknown][14885832] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:20:10.721 [IP Unknown][35971931] Unable to read data from the transport connection: An existing connection was forcibly closed by the remote host.
[2023.06.08] 20:21:20.478 [IP Unknown][65465807] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:21:20.478 [IP Unknown][65465807] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:21:21.078 [IP Unknown][49947022] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:21:21.078 [IP Unknown][49947022] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:21:40.377 [31.94.66.124][41215807] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: An established connection was aborted by the software in your host machine.
[2023.06.08] 20:21:40.377 [31.94.66.124][41215807] StackTrace:    at System.Net.Sockets.NetworkStream.BeginRead(Byte[] buffer, Int32 offset, Int32 size, AsyncCallback callback, Object state)
[2023.06.08]    at System.Net.FixedSizeReader.StartReading()
[2023.06.08]    at System.Net.Security._SslStream.StartFrameHeader(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.StartReading(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.ProcessRead(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.BeginRead(Byte[] buffer, Int32 offset, Int32 count, AsyncCallback asyncCallback, Object asyncState)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.BeginReceive()
[2023.06.08] 20:22:27.021 [IP Unknown][62240187] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:22:27.234 [IP Unknown][16384305] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:22:27.470 [IP Unknown][53828017] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:22:27.549 [IP Unknown][11882326] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:22:27.611 [IP Unknown][28475336] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:22:48.538 [IP Unknown][37315495] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:22:48.538 [IP Unknown][37315495] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:23:38.606 [212.205.99.221][61005936] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: An established connection was aborted by the software in your host machine.
[2023.06.08] 20:23:38.606 [212.205.99.221][61005936] StackTrace:    at System.Net.Sockets.NetworkStream.BeginRead(Byte[] buffer, Int32 offset, Int32 size, AsyncCallback callback, Object state)
[2023.06.08]    at System.Net.FixedSizeReader.StartReading()
[2023.06.08]    at System.Net.Security._SslStream.StartFrameHeader(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.StartReading(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.ProcessRead(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.BeginRead(Byte[] buffer, Int32 offset, Int32 count, AsyncCallback asyncCallback, Object asyncState)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.BeginReceive()
[2023.06.08] 20:23:55.213 [212.205.99.221][22475779] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: An established connection was aborted by the software in your host machine.
[2023.06.08] 20:23:55.213 [212.205.99.221][22475779] StackTrace:    at System.Net.Sockets.NetworkStream.BeginRead(Byte[] buffer, Int32 offset, Int32 size, AsyncCallback callback, Object state)
[2023.06.08]    at System.Net.FixedSizeReader.StartReading()
[2023.06.08]    at System.Net.Security._SslStream.StartFrameHeader(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.StartReading(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.ProcessRead(Byte[] buffer, Int32 offset, Int32 count, AsyncProtocolRequest asyncRequest)
[2023.06.08]    at System.Net.Security._SslStream.BeginRead(Byte[] buffer, Int32 offset, Int32 count, AsyncCallback asyncCallback, Object asyncState)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.BeginReceive()
[2023.06.08] 20:24:16.693 [IP Unknown][42888698] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:24:16.693 [IP Unknown][42888698] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:24:22.090 [IP Unknown][36255229] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:22.121 [IP Unknown][910550] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:22.137 [IP Unknown][30008866] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:22.309 [IP Unknown][5899250] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:22.418 [IP Unknown][2890944] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.447 [IP Unknown][66708467] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.509 [IP Unknown][1154674] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.565 [IP Unknown][12254571] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.633 [IP Unknown][23972625] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.678 [IP Unknown][52814607] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.755 [IP Unknown][27019538] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:23.802 [IP Unknown][38097771] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:24:53.587 [IP Unknown][19368632] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:25:23.608 [IP Unknown][28231457] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:25:43.577 [IP Unknown][27585276] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:25:43.577 [IP Unknown][27585276] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:25:53.698 [IP Unknown][23967334] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:25:53.698 [IP Unknown][11556235] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:26:25.146 [IP Unknown][38168396] Authentication failed because the remote party has closed the transport stream.
[2023.06.08] 20:26:27.159 [IP Unknown][59398760] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:26:28.807 [IP Unknown][40652868] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:26:58.946 [IP Unknown][22432181] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:27:29.038 [IP Unknown][21720377] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:27:37.563 [IP Unknown][12380745] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:27:37.563 [IP Unknown][12380745] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)
[2023.06.08] 20:27:59.243 [IP Unknown][4596186] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:27:59.243 [IP Unknown][29320078] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.08] 20:28:30.567 [IP Unknown][47765509] Exception: (PooledTcpItem.cs) Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
[2023.06.08] 20:28:30.567 [IP Unknown][47765509] StackTrace:    at System.Net.Security.SslState.InternalEndProcessAuthentication(LazyAsyncResult lazyResult)
[2023.06.08]    at System.Net.Security.SslState.EndProcessAuthentication(IAsyncResult result)
[2023.06.08]    at MailService.TcpServerLib.Common.PooledTcpItem.EndConvertToSSL(IAsyncResult asyncResult)

Chris Danks Replied

6/8/2023 at 12:56 PM

I just tried replacing our RapidSSLs with https://portal.smartertools.com/kb/a3466/securing-smartermail-with-lets-encrypt.aspx and the issue remains.

If you guys want to test: https://www.macrumors.com/how-to/download-ios-17-beta-iphone/?fbclid=IwAR10rm4HMAc5Ty-t8mTkkraOvKJ-EWJlr4Uj8Br1nYdMqHAWt7VsQ60XvZU

other than this issue, its almost like a final beta! its very stable and all my apps work including banking which doesn't usually happen with iOS beta's.

Zach Sylvester Replied

6/8/2023 at 1:00 PM

Employee Post

Hello,

Thanks for reaching out again regarding this. I did a little bit of research and it looks like Apple is/has deprecated TLS 1.0 and 1.1 so it might be that happening because you do not have the correct cipher suites installed. From the looks of your logs you may not have TLS 1.2 enabled on the server.

I recommend installing the best practices using the IIS crypto application. https://www.nartac.com/Products/IISCrypto/

After doing this please see if it starts working.

Thanks,

Zach Sylvester Software Developer SmarterTools Inc. www.smartertools.com

Chris Danks Replied

6/9/2023 at 1:22 AM

This is what I see:

also the issue is when SSL is off (port 143)

Gabriele Maoret - SERSIS Replied

6/9/2023 at 1:44 AM

Have you tried to make a backup of the configuration (under "Advanced") and then apply the best practices (with the appropriate "Best Practices" button at the bottom left)?

Of course you have to apply the new settings with the "Apply" button (bottom right) and then restart the server...

Gabriele Maoret - Head of SysAdmins at SERSIS Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)

Chris Danks Replied

6/9/2023 at 3:10 PM

Even though this issue is also effecting none SSL would TLS still be the cause??

Gabriele Maoret - SERSIS Replied

6/10/2023 at 1:03 AM

Maybe it can be, because SSL and old TLS versions are deprecated by Apple and thus it can lead to a strange behaviour with their products...

Either way, it doesn't hurt to give it a try...

Chris Danks Replied

6/10/2023 at 3:37 PM

Hi guys

I did this tonight and rebooted the server, IMAP still not working. SMTP is not effected as i can send email from iOS/iPad OS 17 but not receive on IMAP.

Chris Danks Replied

6/10/2023 at 3:51 PM

I just checked logs

[2023.06.10] 23:46:20.627 [IP Unknown][50208048] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:20.627 [IP Unknown][58483356] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:40.119 [IP Unknown][42484335] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:46.797 [IP Unknown][44002640] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:47.127 [IP Unknown][44430263] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:47.315 [IP Unknown][1296398] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:47.487 [IP Unknown][7697324] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:47.724 [IP Unknown][28917419] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:48.558 [IP Unknown][2741287] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:48.589 [IP Unknown][37797744] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:46:49.622 [IP Unknown][5948721] Authentication failed because the remote party has closed the transport stream.
[2023.06.10] 23:47:10.421 [IP Unknown][21309594] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:47:18.699 [IP Unknown][27765407] A call to SSPI failed, due to someone connecting with an unsupported TLS version.
[2023.06.10] 23:47:18.714 [IP Unknown][42528722] A call to SSPI failed, due to someone connecting with an unsupported TLS version.

even though privacy is turned off in iOS its still showing unknown so that could be an IOS beta bug.

The unsupported TLS I‘d of expected to go after making the changes earlier.

This is the TLS config now since rebooting:

And smartermail isn’t using any overrides for SSL/TLS:

Christopher Glasgow Replied

6/10/2023 at 5:17 PM

I am having the same issues, with TLS 1.0 and 1.1 off.

Chris Danks Replied

6/11/2023 at 11:05 AM

I'm glad its not just me!

I opened a ticket with smartertools on thursday, hopefully someone will see it soon and reply

Dave McLelland Replied

6/12/2023 at 10:17 AM

I had a client install the iOS Developer Build 17 on his device and he is reporting the same issue. Following this thread...

Zach Sylvester Replied

6/12/2023 at 10:18 AM

Employee Post

Hello,

I'm installing the IOS 17 dev build on our test IPad right now. I'll let you guys know what I find.

Thanks,

Zach Sylvester Software Developer SmarterTools Inc. www.smartertools.com

Zach Sylvester Replied

6/12/2023 at 10:38 AM

Employee Post

Hello,

Just following up. I was able to replicate this issue. I have sent it over to the developers. We will provide updates on this thread as they come.

Thanks,

Zach Sylvester Software Developer SmarterTools Inc. www.smartertools.com

Zach Sylvester Replied

6/14/2023 at 7:16 AM

Employee Post

Hello,

I wanted to provide you with an update regarding the IOS 17 issue. Our developers have investigated and determined that the problem lies within the current version of iOS 17. It has come to our attention that if you test this with an exchange server, you will encounter the same issue. Therefore, it is now in the hands of Apple to address and resolve this matter.

In light of this new information, I will be adjusting the status of this issue from "being fixed" to "Known." Moving forward, we will continue monitoring the situation and strive to eventually reclassify it as "not a problem."

Thank you for your understanding and patience.

Best regards,

Zach Sylvester Software Developer SmarterTools Inc. www.smartertools.com