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What password for loading certificate?
Question asked by Thomas Leylan - 4/13/2025 at 12:03 PM
Answered
This seems to have started happening an update (or two ago) but now I have to redeploy the .pfx file every day. Ultimately I get the following message: Certificate cannot be loaded with password provided

At the moment I still see the .pfx file (I just redeployed it) but it will disappear tomorrow. The problem I have is with all the passwords and such I don't know which password is being complained about and/or who is complaining.

I'm using Certify The Web that uses Let's Encrypt to generate the cert. Have no problems with the cert or anything else for a few years. CTW runs a deployment script which simply copies the file. It works when I tell it to redeploy but as you can see there is some sort of issue loading it. I can check my email at the moment regardless BTW.

How do I find out which password and where to enter it?
K
Kyle Kerst Replied
4/14/2025 at 4:52 PM
Employee Post
The password we use to access the PFX files is entered under Settings>SSL Certificates when logged in as a system administrator, and that password should match the one you have set up in your deployment script where it exports the newly renewed certificate to PFX format. If you can find the password for that script/export configuration and copy it over to SmarterMail that should get you back into those certificates. 
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
Thomas Leylan Replied
4/14/2025 at 5:55 PM
Thanks for that. I am logged in right now as the admin. I edit the Certificate Password (tried pasting it and typing it) and the Save button is never enabled.

I can BTW edit other items in General, Protocols and such and the Save button enables in those cases. Cancel button enables as I enter the password.
Tony Scholz Replied
4/15/2025 at 9:20 AM
Employee Post Marked As Answer
Thomas, 

Enable the switch for "Enable Automated Certificates", if you see any fields in RED you will need to fix them, and once done you can disable "Enable Automated Certificates" and save. 
Tony Scholz
Lead Network/System Administrator
SmarterTools Inc.
K
Kyle Kerst Replied
4/15/2025 at 9:40 AM
Employee Post
As Tony pointed out that usually means there is some setting on that page that is failing validation preventing the save button. The other thing I've seen give people trouble is the browser auto-fill behavior for passwords where the browser forcefully replaces the password you've entered with a saved one from it's memory, this could also prevent saving if the value its submitting is invalid. 
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
Thomas Leylan Replied
4/15/2025 at 10:26 AM
I think we can agree that is counter-intuitive but it worked (for the most part). It showed the couldn't load message so I had Certify The Web deploy the file again. Though there was only one file in the folder SM showed 2 certificates. One it could load and one with the error message displayed.

No amount of messing with the check boxes permitted me to remove the bogus one. So I deleted the files intending to copy them once again.

I thought I would try to remove the bogus message from SM and I pressed the Choose File button on a dialog having entered no password. I now have a spinner running with a Next button visible but everything is disabled. If a required input is missing I would have thought it wouldn't proceed. The site is pretty much hosed and disabled though my browser will step back. I just exited out of the site.

Ok back in and it shows no certificates which is expected. Deployed the cert and it shows 1 cert and it is active so I think all is well again.

Thanks for the assistance. I understand very well how making things obvious for every user is an impossible task but this was a bit more mysterious than it probably needed to be.

Thanks again.
K
Kyle Kerst Replied
4/17/2025 at 7:19 AM
Employee Post
Glad to hear you were able to get this resolved Thomas. I'll note your feedback with our development team as we're always trying to improve the user experience overall.
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
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