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TOPIC: TechTool Protection had a problem sending alert email.

TechTool Protection had a problem sending alert email. 19 May 2019 04:02 #11087

Hi.

I have an ongoing problem with TechTool Protection trying to send email notifications. Assuming I have the right password, I get the error message: "TechTool Protection had a problem sending alert email. (07) SMTP Server --> 500 command unrecognized". Is this a problem with TTP or with my email account/program/password? Currently running TTP 11.0.3 on iMac 2008 (B&W) with OSX 10.11,6 (El Capitan). Any suggestions would be appreciated. THANKS!
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TechTool Protection had a problem sending alert email. 19 May 2019 12:14 #11088

Please send a screen capture of the way you have your Email Alerts pane configured, showing the servers and ports, and the account name, to This email address is being protected from spambots. You need JavaScript enabled to view it. . You will receive a reply by email. Thank you.

In some cases, the problem is the port number, and in others, adding or removing the domain name from the account name works.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 20 May 2019 05:32 #11093

Hi. Thanks for your prompt response. Enclosed is a screen-shot of the TechTool Protection email settings. I can't see the attachment in the Preview. I've tried 3 times, but still can't see it. I'm assuming the file is attached. Thanks for the help!
Last Edit: 20 May 2019 09:59 by micromattech3.
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TechTool Protection had a problem sending alert email. 20 May 2019 10:01 #11094

You are welcome.

Please send the screen capture to This email address is being protected from spambots. You need JavaScript enabled to view it. . I cannot have it posted here, because it has your email address in it, and you may get a lot of spam as a result.

You should find out what port is recommended by your ISP. Port 25 is usually blocked by any ISP by default, as part of their spam reduction efforts.
MicroMat Inc
Makers of TechTool
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The following user(s) said Thank You: rprochot

TechTool Protection had a problem sending alert email. 21 May 2019 20:05 #11103

After many years of trying to send email alerts, and failing, I just found the answer:

Port 25 is monitored for SPAM. According to my ISP it does not require Authentication.
When I removed the Check-mark for "Use SMTP Authentication" The email alert was sent just fine.

THANK YOU!
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TechTool Protection had a problem sending alert email. 21 May 2019 20:19 #11104

i am using Port 25 (By Default). A LONG and more COMPLETE ANSWER:

According to my ISP:
"For sending, there is no authentication on port 25.
Otherwise you'd want to use the following setting if wanting to use authentication on sending...
Outgoing Mail Server: mail.(INSERT ISP SERVER HERE).(COUNTRY EXTENSION HERE) - Eg. "mail.bestprogram.ca"
Server Type: SMTP
SSL: on
Port: 587
Authentication: Plain Text or Password
With this authenticated method, the user name is email address without @bestprogram.ca, and then your password.

You can try with authentication disabled, and leave it on port 25. Or change to the provided information above to use with authentication."

Hope this helps some-one else with a the same issues. THANKS for all your help.
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TechTool Protection had a problem sending alert email. 21 May 2019 21:24 #11105

You are welcome, and thanks for both of your last postings. I will forward the details provided by your ISP to the beta administrator for TechTool Pro.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 22 May 2019 06:19 #11106

Again, THANKS for your help, and for leading me to my ISP.
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TechTool Protection had a problem sending alert email. 22 May 2019 10:09 #11107

You are welcome, and the beta administrator for TechTool Pro was pleased to get the information you provided regarding your ISP. Thanks again.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jun 2019 23:21 #11206

None of these options as presented do not work. I have tried all the options Apple gave me and all the options Comcast gave me. No luck. Will seriously consider not investing any more money as this has been an ongoing issue for me for over a year.
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TechTool Protection had a problem sending alert email. 22 Jun 2019 02:10 #11207

Please send a screen capture of the way you have your Email Alerts set up in the TechTool Protection system preferences pane to This email address is being protected from spambots. You need JavaScript enabled to view it. . You will receive a reply by email on Monday. Thank you.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 20 Oct 2019 20:25 #11475

I am getting an error message whenever TTP 11 tries to send to send out an email alert. It says "SMTP timeout waiting for server ready.

Just guessing at the reason: I have no problems with email alerts working or sending email using the same server settings on other programs. I know my email server could possibly be a little slow because it is on a shared system (currently hosted on GoDaddy). Is there any way to increase the default timeout waiting period so I can test if that is the problem? Would it help to use a non-secure outgoing email?
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TechTool Protection had a problem sending alert email. 20 Oct 2019 21:10 #11476

Thanks for your clear and detailed report, and for removing your email address from the screen capture.

I have not encounter this particular error before, and suspect that a programmer may have to look at a log file to see what might be done to solve the problem. Please send a message to This email address is being protected from spambots. You need JavaScript enabled to view it. . You will receive a reply by email on Monday. Thank you.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 26 Oct 2019 05:25 #11483

I do have the same trouble with Gmail. I changed the App password, but it didn't work.
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TechTool Protection had a problem sending alert email. 26 Oct 2019 12:35 #11484

Please send a screen capture of the way your have the Email alerts feature configured to This email address is being protected from spambots. You need JavaScript enabled to view it. . You will receive a reply by email on Monday. Thank you.

Your ISP can tell you what port you should be using. It is the same one that Apple Mail would use.
MicroMat Inc
Makers of TechTool
Last Edit: 26 Oct 2019 13:34 by micromattech3.
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TechTool Protection had a problem sending alert email. 21 Jan 2020 00:53 #11773

Hi

I am getting the same error message whenever TTP 11 tries to send to send out an email alert.

It says "SMTP timeout waiting for server ready.

I sent an email today with a screenshot of my set up.

Hopefully you can help me solve this mystery.

Ty
Wazzjazz
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TechTool Protection had a problem sending alert email. 21 Jan 2020 01:19 #11774

Thanks for your report and your cooperation. As mentioned earlier, you may need to contact your ISP to find out what port should be used for outgoing mail.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jan 2020 01:26 #11775

Hi, I contacted my ISP and they told me port 465 which I entered into your software. Only to get the error message reported

"SMTP timeout waiting for server ready.

The ISP requires two factory authentication so I set up and app password and I still get the same message when I use this password.

Any suggestions?

Wazzjazz
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TechTool Protection had a problem sending alert email. 21 Jan 2020 01:38 #11776

The only suggestion I can make is to find out whether SSL or TLS authentication is required. If it is not, then uncheck that box. Some email services do not support those authentications.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jan 2020 01:48 #11777

Hi According to Rogers.com (ISP) SSL/TLS is required.

This might have something to do with the two factor authentication.

Have you had any reported issues when the ISP requires two factor authentication?
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TechTool Protection had a problem sending alert email. 21 Jan 2020 01:57 #11778

I am going to have to ask about that tomorrow.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jan 2020 02:04 #11779

We have a Knowledge Base article about email alerts with two-factor authentication, but I suspect you have already done what is suggested in the article.

The Knowledge Base article is at www.micromat.com/support/knowledge-base/...or-authentication-12
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jan 2020 02:13 #11780

Hi, I did review this and I am not using a gmail or an iCloud email account so I do not think it applies.

Regards
Wazzjazz
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TechTool Protection had a problem sending alert email. 21 Jan 2020 02:17 #11781

Thanks for the update, and I hope this issue will be able to be solved tomorrow. You may need to have your ISP help you with the two-factor authentication. iCloud and Gmail are just two of the services that require it.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jan 2020 06:21 #11782

I have my email accounts on a mail server under a web domain that I personally administrate. Somehow, the alerts email I have been using with Micromat and Tech Tool Pro for 15 years, just stopped working for TTP Email Alerts in late 2019 (TTP gives me a server timeout error). Nothing that I am aware of had changed except perhaps that my web hosting company, Go Daddy, may have moved my account onto a different physical server platform. I am not aware of any problems with any of my emails being sent through any other application or service.

I have consumed far too many cycles trying to figure out what could be causing this problem. I changed no settings on my email account, server or in TechTool Protection, and previously had this TTP email alerting feature working flawlessly for many years. I am able to successfully add my TTP alerts email to other programs and email clients and have consistently sent and received email messages through several platforms using that email account (all with the same SMTP settings). Though the good people at Micromat have looked at my log files and vaguely suggested what I might do to resolve the problem, there appears to be no straightforward solution. If you are still at your wits' end trying to get this feature to resume working, I suggest you just disable TTP Email Alerts indefinitely and save yourself further frustration.
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The following user(s) said Thank You: jk#3

TechTool Protection had a problem sending alert email. 21 Jan 2020 23:21 #11789

Plz check out my conversation last year, in the forum, last year here: <<LNK: <www.micromat.com/component/kunena/techto...ng-alert-email#11104>

More elongated answer will follow.
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TechTool Protection had a problem sending alert email. 21 Jan 2020 23:26 #11790

Thanks for posting the link to your contribution to this subject.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 21 Jan 2020 23:30 #11791

I hope I'm nit breaching protocol, but I'm not sure how to link to my previous discussions regarding this subject last year, so here it is in a nut shell (SORRY FOR THE DUPLICATE POSTING):

1) After many years of TTP trying to send email alerts, and failing, I just found the answer:

Port 25 is monitored for SPAM. According to my ISP it does not require Authentication.
When I removed the Check-mark for "Use SMTP Authentication" The email alert was sent just fine.

2) i am using Port 25 (By Default). A LONG and more COMPLETE ANSWER:

According to my ISP:
"For sending, there is no authentication on port 25.
Otherwise you'd want to use the following setting if wanting to use authentication on sending...
Outgoing Mail Server: mail.(INSERT ISP SERVER HERE).(COUNTRY EXTENSION HERE) - Eg. "mail.bestprogram.ca"
Server Type: SMTP
SSL: on
Port: 587
Authentication: Plain Text or Password
With this authenticated method, the user name is email address without @bestprogram.ca, and then your password.

You can try with authentication disabled, and leave it on port 25. Or change to the provided information above to use with authentication."

Hope this helps some-one else with a the same issues.
THANKS to Micromat Tech Support & this forum for ALL your help. (I've has no problems in the past year & TTP is working GREAT!)
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TechTool Protection had a problem sending alert email. 21 Jan 2020 23:35 #11792

PS - FYI: I am running a 24" Early 2008 iMac w. 2.8 GHz Processor & OSX 10.11.6;
TTP Version 11.0.5
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TechTool Protection had a problem sending alert email. 21 Jan 2020 23:37 #11793

You are welcome! I spent years trying to resolve it.
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TechTool Protection had a problem sending alert email. 21 Jan 2020 23:45 #11794

Thanks for updating this thread with the solution you and your ISP worked out.

I am surprised that your ISP lets you use Port 25. Many ISPs block it by default for sending email. They must trust you are not a spammer.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 22 Jan 2020 00:23 #11795

Thank you rprochot, your post solved my issue when both my ISP and tech support could not.

Thanks again.

Wazzjazz
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TechTool Protection had a problem sending alert email. 22 Jan 2020 01:49 #11796

Glad to help. It's a nice feeling to be able to provide some useful input after almost 30 years of receiving help from the many participants of this forum. Once again: THANK YOU ALL!
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TechTool Protection had a problem sending alert email. 16 Mar 2020 20:01 #11875

I was also frustrated by this error message. But found a solution, and what I suspect is a bug. TechTool protection is somehow swapping ports 465 and 587 internally.

If your SMTP server is listening on port 465, but timing out, try using port 587....

If your SMTP server is listening on port 587, but timing out, try using port 465....

Putting the incorrect port number into TTP's settings fixed the issue for me, on 2 different computers one with v11 one with v12.

Cheers!
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TechTool Protection had a problem sending alert email. 16 Mar 2020 20:03 #11876

See my post below, TTP is swapping port 587 and 465..... if you enter 465 it uses 587 and vice versa.
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TechTool Protection had a problem sending alert email. 16 Mar 2020 20:15 #11877

Thanks for your report. That is very odd behavior.

Please send a message to This email address is being protected from spambots. You need JavaScript enabled to view it. with your findings. You will receive a reply by email, and may be asked to send in some additional information. Thank you.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 16 Mar 2020 20:28 #11878

I have communicated with tech support on this......I agree it's weird behavior, but I've confirmed the problem and solution on 4 different machines, all on different OSX versions and with TechTool Pro versions 7, 11, 12.

All my other email software refuses to connect if I swap port 465 for port 587 except for Tech Tool protection, which will not work unless I do........

All my machines are now sending email just fine with this workaround.
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TechTool Protection had a problem sending alert email. 16 Mar 2020 20:32 #11879

Thanks for the additional details.

I hope that we will be able to determine why you are experiencing this odd behavior, and thanks for your investigative efforts, patience and cooperation.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 17 Mar 2020 01:01 #11880

I appreciate y'all working on it. My solution worked due to port 587 being setup with lower security on the server, NOT because TTP is swapping the numbers like I expressed.... my testing was not deep enough. Still have no idea why the secure port 465 cannot connect and times out "waiting"........while the unsecure port 587 works...
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TechTool Protection had a problem sending alert email. 17 Mar 2020 01:21 #11881

Thanks for the clarification, which I hope you have passed along to This email address is being protected from spambots. You need JavaScript enabled to view it. .

I suggest you ask your ISP if they have any idea why you are getting the time outs on port 465. They may have encountered this issue before.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 17 Mar 2020 01:46 #11882

I did pass along to help....

And I'll ask my ISP, but to reiterate, all my other apps that use smtp are having no trouble with port 465 at all, it's just the TTP control panel's email app that's having the trouble.
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TechTool Protection had a problem sending alert email. 17 Mar 2020 01:50 #11883

Thanks again for your cooperation, and I hope we will have an explanation soon.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 30 Mar 2020 16:36 #11914

I'm experiencing precisely the same problem as others configuring TechTool Protection > Email Alerts > SMTP Server.

MANY attempts to "Use SSL/TLS" with port 465 all fail with "SMTP timeout waiting for server ready." macOS Mail NEVER has this timeout problem.

Changing the Port Number from 465 to 587 (with "Use SSL/TLS" enabled or disabled) results in a successful "Send Test E-mail."

I'm reluctantly using this insecure, non-SSL workaround because it's important for TechTool Protection to inform me of problems.

I'm using TechTool Protection 12.0.2 on macOS 10.13.6.
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TechTool Protection had a problem sending alert email. 30 Mar 2020 19:06 #11915

Thanks for your report.

You stated:

Changing the Port Number from 465 to 587 (with "Use SSL/TLS" enabled or disabled) results in a successful "Send Test E-mail."

If so, I do not see why there is a problem with using the combination of port 587 and "Use SSL/TLS" enabled, since you reported that it worked. I am sorry if I misinterpreted what you wrote.
MicroMat Inc
Makers of TechTool
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TechTool Protection had a problem sending alert email. 30 Mar 2020 19:22 #11916

Thanks @micromattech3 for your speedy response to my report.

I should have mentioned that my hosting service strongly recommends using SSL/TLS to connect to its SMTP server (to shield my account & password from network sniffers).

Although I can configure TechTool Protection's SMTP setting to "Use SSL/TLS" with a non-SSL port, I'm concerned that SSL is ignored on port 587 (as others have suggested).
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TechTool Protection had a problem sending alert email. 30 Mar 2020 19:33 #11917

You are welcome, and thanks for mentioning the issue of port 587 being ignored by SSL.

I think you should ask your ISP if they ignore port 587 with SSL, because Apple still recommends using it for iCloud email, and they do not raise the "ignoring" issue:

Mail server settings for iCloud email clients

Published Date: February 27, 2020
MicroMat Inc
Makers of TechTool
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