Use this to Generate a Command for Open SSL e.g the below 

https://www.digicert.com/easy-csr/openssl.htm

openssl req -new -newkey rsa:2048 -nodes -out test_test_com.csr -keyout test_test_com.key -subj "/C=US/ST=Test/L=/O=Test/CN=test.test.com" 

Now add to the end : -config “C:\Program Files\Autonomy\WorkSite\Apache\conf\openssl.cnf”

In Comand Prompt Navigate to Openssl.exe (  C:\Program Files\Autonomy\WorkSite\Apache\bin ) 

Run the full command

openssl req -new -newkey rsa:2048 -nodes -out test_test_com.csr -keyout test_test_com.key -subj "/C=US/ST=Test/L=/O=Test/CN=test.test.com" -config "C:\Program Files\Autonomy\WorkSite\Apache\conf\openssl.cnf"

It will generate a .csr and a .key file , copy these to C:\SSL

Use the CSR with your certificate Authority to Generate a .crt file and also a chain file

Download these to C:\SSL

Open the file : C:\Program Files\Autonomy\WorkSite\Apache\conf\worksite.conf

Add or Change the Lines to the below

SSLCertificateFile “C:\SSL\certs_test_test_com.crt”
SSLCertificateKeyFile “C:\SSL\test_test_com.key”
SSLCertificateChainFile “C:\SSL\certs_DigiCertCA.crt”

Restart iManage Work Server Service

Next

Copy “C:\SSL\test_test_com.key” to “C:\SSL\test_test_comkey.pem”

Open certs_test_test_com.crt with Notepad and copy the contents into a new file

Open certs_DigiCertCA.crt with Notepad and copy the contents to the below of the new file ( directly under the other certificate on a new Line ) 

Save this as C:\SSL\test_test_comfullchain.pem

On the Worksite Service Properties  , Configure Hosted DM

Change .PEM files to your new file

Restart iManageMicroServiceHub Service