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Sunday, September 19, 2021

Renewing A Public Cert On A Totemomail Encryption Gateway

This isn't technically an Exchange article. but for those unfortunate admins that are unlucky enough to have been forced by management to run a Totemomail Encryption Gateway in their environment, this post will show you how to renew your public certificate.

The reason I'm writing this is because Totemo makes ZERO resources available to the public on how to manage this terrible product and they force you to open a ticket for everything...job security I guess.

Unlike most other appliances, web servers, etc. the cert request process on the Totemo Gateway doesn't include the private key, which is needed later for the new cert import. You'd think if it were required for the import, it would be included in the request, but as I said above, the product is garbage.

So you need to export the private key manually and then jump through some hoops to merge it with your new cert from your CA; that requires some OpenSSL work, which is a bit of a pain.

First, start your cert request. 

Expand Certificates > Own Server Certificates > hit the "New HTTPS cert" button.

Totemo Certs


Totemo CRL

Fill out your org info and download/save the req on your local machine.

Totemo CRL Info

Send the req to your public CA and you should get a cert.cer and intermediate.pem back.

Next, export the private key

**Note** The private key is stored in the Totemo database (either locally or in a standalone DB, depending on how you have it set up)

You can export the private key from your current HTTPS cert or from a current user.

To export the private key from the current HTTPS cert, Expand Certificates > Own Server Certificates

Click the cert icon > go to the Details tab > hit the "export with pr. key" button

Totemo Own Cert
Totemo Export Key

Enter your first and second "four eyes password"

Enter your password that will be set on the private key file, twice

Hit "Download"


Totemo Export Key Password

To export the private key from a user, expand User Management > Users.

Totemo Users

Click the certificate management (keys icon) for an active user > click the cert icon > Details tab > "export with pr. key" button

Totemo Users Key

Totemo Users Cert

Totemo Export Users Cert


Enter your first and second  "four eyes password"

Enter your password that will be set on the private key file, twice

Hit "Download"

A gotcha here: make sure you use a strong password on the export (capital, lowercase, number and special character, and at least 8 characters long). There is no "help" prompt on the Totemo for this, it just throws a stupid error that says "error connecting to database" which doesn't mean anything at all.

***Note*** In order for the "export with pr. key" button to be visible in the above steps, you first need to set your "Four Eyes Password" under the Four Eyes Password section...set both passwords; they can be anything, but make them strong. If they haven't been set yet, leave the box empty and hit the "Continue" button to set them.

Totemo Four Eyes

Totemo Four Eyes Password

Once you have your private key exported, fire up OpenSSL, which should be located in C:\Program Files\OpenSSL-Win64

If you don't have it installed you can grab it from here 

First we need to extract the key file. Copy your privatekey.p12 file to the C:\Program Files\OpenSSL-Win64\bin directory then run the following command:

openssl pkcs12 -in privatekey.p12 -out totemokey.key -nodes -nocerts

***Note*** Change privatekey.p12 to the filename of your p12

Next, copy your totemokey.key, cert.crt and intermediate.pem files to the C:\Program Files\OpenSSL-Win64\bin directory

Now we'll merge the files by running the following command:

openssl pkcs12 -export -out totemo.pfx -inkey totemokey.key -in cert.crt -certfile ntermediate.pem

***Note*** Change to totemo.pfx, totemokey.key, cert.crt, ntermediate.pem to the filenames of your certs

You will be prompted to create a password; this can be anything, but I suggest make it strong.

Once it completes, you will have a brand new pfx file, which you will import into the Totemo

Expand Certificates > Own Server Certificates

In the dropdown, select "Import certificate for HTTPS"

Hit the "choose file" button and select your new .pfx

Enter your password you set on the pfx in OpenSSL

Hit OK

Totemo Import Cert

If it goes correctly, it will list your new cert.

Totemo New Cert

You can now delete your old cert and the cert req and reboot the webmail service...that's required or else the old cert will still be assigned to the services (which is stupid).

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