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mackov83

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I recently started configuring PasswordState to send emails out. I have the following configuration in place:

 

image.png.2c72292221ab4c25995f0fcf57820924.png

 

The settings above map to an Azure AD application called Passwordstate, and I have given permissions for this application to send as any user:

image.png.49036a6e42028825a20f7aa9316c54fd.png

 

I can successfully receive test emails as proven below:

 

Test email from Passwordstate.

If you have received this email, but are still not receiving other emails from Passwordstate as expected, you can check the following things:

1. Check to see if there are any 'Email Templates' disabled
2. Check to see if there are any disabled emails for 'Email Notification Groups'
3. Check to see if the user has disabled email notifications as per their 'Preferences'
4. Check with Application Event Log on your web server for any errors.

 

No matter what I do, I cannot receive emails from Passwordstate actions as I should be. Are there any other reasons why this would fail if the test emails are successful? I have followed through the steps in the manual, as well as the troubleshooting steps in the test email (as shown above).

 

For the record I am on build 9665 and I don't see any fixes for this in 9700...

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I should that the account being used to send the emails is a sharedmailbox account. However, when replacing that with my own email account (which is Global Admin) the emails are also not received. As you can also see I checked the box to 'Save Emails to Sent Items'. There is nothing being recorded as sent in this mailbox, except for the test emails.

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Hi, I have done a lot of digging into this and would be very interested to get feedback from ClickStudios about my findings...

 

Please refer to following screenshot:


image.png.0c5a637550f1fb60d012f270eaeda9c7.png

 

As this was a new implementation, I had zero settings in place for SMTP (number 3) and reading the documentation I expect this should be correct. After all, when you click the drop-down menu (number 1) it is Either Exchange Online or SMTP. So I should only need to configure one or the other right?

 

As I don't have an SMTP server (or relay) in my case and with security in mind, Exchange Online using OAUTH seems the best approach. With Exchange Online details (number 2) only configured results were:

  • Test emails = successful
  • Self destruct = successful
  • Email templates = failure, and testing not available (see further down)
  • SMTP Email Test = failure (expected as not configured)

 

Out of curiosity, I added the SMTP settings for outlook.office.com, specified the TLS port 587, and entered the same shared mailbox - this time as the name (unlike for Exchange Online which is an Object ID). Results with the extra SMTP config in place:

  • Test emails = successful
  • Self destruct = successful
  • Email templates = successful (progress!)
  • SMTP Test = failure (more or less expected as only a partial config)

 

As mentioned earlier, the Test Email button is greyed out for all Email Templates unless you specify SMTP details:

 

image.thumb.png.c08da23308801ac36c3944e0f66ec7e6.png

 

Conclusions:

  1. Documentation clearly requires some updates - not enough detail regarding email configuration unless I am reading the wrong one: Passwordstate Security Administrators Manual (clickstudios.com.au). I suspect it is correct as the detail around O365 configuration is all there.
  2. It seems that Email Templates rely on SMTP configuration in order to work - surely this should not be the case and needs to be fixed?

 

P.S. I will state that I do use CodeTwo for email signatures, though the shared mailbox that I am using to send emails has been disabled from having an email signature applied. Just in case there are known issues with CodeTwo.

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@support at this point I am using the Passwordstate free version as I am a small business of one person. As a result, I don't believe I get support for your product?

 

For the record, I think your product is fantastic and has many more features that the likes of LastPass, Bitwarden etc. I have used it for years in a previous company which is why I am using it now, though I have learnt much more about it recently having had my own instance to experiment with.  

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Hello mackov83,

 

Yes, unfortunately technical support only comes with the paid version of Passwordstate. We wish we were resourced to provide support for the free version, but we do have thousands of customers using the free version.

 

We will look into your points above for the next build though.

 

Regards

Click Studios

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  • 3 weeks later...

@support 

 

In build 9708 changelog you mention the following: "Fixed an issue on the Email Templates screen where it was not possible to test templates when using Exchange Online email option".

 

I would say that this is not properly fixed and you still have some flaws. While I no longer have to specify the SMTP 'Server Host Name' if you also remove the 'Send From Email Address' value in the SMTP configuration, you now end up with the following error:

image.png.0ffda69acb672805029004ea1f6a0ad1.png

 

As I mentioned previously, Exchange Online and SMTP should be two completely independent options. When using Exchange Online exclusively, there should be no reliance on any SMTP configuration. 

 

At least this is the case with build 9715.

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  • 2 weeks later...

Hi Support,

 

This build has resolved the need to enter the server name, however, test emails sent from email templates are not sent or delivered according to Exchange Online message trace function. Passwordstate however shows a black banner at the bottom of the screen stating the email has been successfully sent.

 

Test emails triggered from the Exchange Online system settings are working. Therefore, this continues to look like the email templates were hard coded for SMTP and the fixes being put in place are slowly removing these barriers.

 

It does however make me question your testing procedures. It seems you only fix the issues being highlighted without testing the entire flow...

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Hello,

 

To confirm, the only issue you're having is testing sending emails from the Email Template screen, and all other functionality is working?

 

If so, we'll revisit this again in the next build. As testing these templates is not critical to the software, it will be a while before next build. But if there is something more critical we're not aware of, please let us know.

Regards

Click Studios

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After removing SMTP details Email notifications have stopped completely - as they are based on the email templates. From what I have seen, if the "Email Test" on the templates fails, email notifications do not work.

 

The only way that I have found that allows the test emails to be sent successfully (without SMTP settings) from within the templates is to specify a delivery address as per below:

 

image.png.c9fbcae6af287759e0280fba2598ec28.png

 

To be clear:

  1. All users have an email address visible in Passwordstate
  2. With SMTP settings specified, emails work as expected
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Hello, we believe we've figured out the issues this time, which will be fixed in the next release.

The reason we did not pick it up in our testing, was because we left behind some SMTP settings, instead of clearing them. As a work around for now, you can make this work:

  • By having something in the SMTP mail server setting whilst using Exchange Online as the mail option
  • By having an email address in Also Send Emails To section on the Email Templates page.

Thanks again for reporting it, and for your patience.

Regards

Click Studios

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Thanks for the update, I look forward to the next release and hopefully this is resolved for good.

 

I did mention multiple times in this thread that Exchange Online and SMTP should be completely independent of one another. Therefore, I find it a little strange that you would leave the SMTP details in place during testing. As an independent contractor with my own business, if you want to hire me for testing I would be open to it :)

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Hello,

 

I tested this, separate to the other developer, and it's working for me.

I've ensured no SMTP settings were set, and tested the Email Templates, Self Destruct Messages, and various functionality where the Passwordstate Windows Service sends emails.

Have you selected the option to "Save Emails to Sent Items"? If so, in Exchange Online, does it say it's sent the email or not?

Regards

Click Studios

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Yes, I had "Save Emails to Sent Items" enabled so that I could tell whether the messages were being received by the sending mailbox or not.

 

It appears like it could be working now. I will wait and see later today whether emails are still being received. I believe one of the services sometimes needs restarting which can impact mail settings? From what I remember it updates every 5 minutes by default?

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Hello mackov83,

 

Using the Test buttons, sends emails live from the UI - so it doesn't add records into the QueuedEmail table, for the Passwordstate Windows Service to send.

The Windows Service will pick up any settings changes within 5 minutes, but as you configured your settings quite some time ago, this would not be relevant. Plus, upgrading Passwordstate also restarts the Passwordstate Windows Service.

 

If you see items in Sent Items, and are not receiving them, then possibly check your spam folder - the test Email Template email for me was caught by our spam software.

Regards

Click Studios

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