Copy SSL Certificate from Apache Server to Windows Server
Moving an SSL certificate from Apache to Windows Server requires specific steps to ensure secure data transfer. SSL certificate migration between servers helps maintain website security and prevents service interruptions.
This guide explains the process of exporting your SSL certificate from Apache, converting it to the correct format, and importing it into Windows Server. The transfer involves handling certificate files, private keys, and proper configuration settings.
You will need to access both servers, gather required certificate files, and follow security protocols during the migration. This process maintains your website’s HTTPS functionality and keeps user data protected. The steps outlined here work for most standard SSL certificates used on Apache and Windows servers.
A Basic Steps of the SSL Certificate Migration Process
Here is an overview of the main steps involved in migrating an SSL certificate from Apache to Windows:
- On the Apache server, export the SSL certificate and private key into a PKCS#12 file. This bundles the certificate and key together.
- Convert the PKCS#12 file into a PFX file. This is a format recognized by Windows servers.
- Securely transfer the PFX file to the Windows server.
- Import the PFX file into the Windows server and configure SSL bindings.
- Update DNS records to point to the new Windows server.
- Test the SSL certificate on the Windows server to ensure traffic is encrypted.
- Decommission the certificate on the Apache server once the migration is complete.
Step 1: Export the SSL Certificate and Private Key from the Apache Server
The first step is to export the SSL certificate and its private key from the current Apache server. This bundles the certificate and key into a single file that can be imported into the new Windows server.
Here are the details on exporting the certificate and key on Apache:
- The OpenSSL toolkit must be installed on the Apache server to access the commands to export the certificate and key. OpenSSL is usually included with Apache but can be installed separately if needed.
- Use the OpenSSL pkcs12 command to export the certificate and key to a PKCS#12 file. For example:
openssl pkcs12 -export -in /etc/ssl/certs/mycert.crt -inkey /etc/ssl/private/mycert.key -out mycert.p12
- Create a secure passphrase to protect the PKCS#12 file when prompted. This will be needed later when importing it into Windows.
- The command exports mycert.crt and mycert.key into a bundled mycert.p12 file secured with the passphrase.
- Verify the file was created in the current directory and safely back it up.
This exports the certificate and key from Apache into a PKCS#12 file that can be transferred to the Windows server.
Step 2: Convert the PKCS#12 File into PFX Format for Windows
The PKCS#12 file exported from Apache must be converted to Microsoft’s PFX format before being imported into Windows.
Here is how to convert from PKCS#12 to PFX using OpenSSL Command:
- OpenSSL must be installed to use the pkcs12 command. If it is not already included in your system, install it first.
- Use the following OpenSSL command to convert PKCS#12 to PFX:
openssl pkcs12 -in mycert.p12 -out mycert.pfx
- Enter the passphrase used to secure the original PKCS#12 file when prompted.
- The command converts mycert.p12 into a mycert.pfx file compatible with Windows servers.
- Verify the PFX file was created, make a backup copy, and safely transfer it to the Windows server.
Converting the certificate and key into PFX format prepares the file for importing into the Windows server.
Step 3: Securely Transfer the PFX File to the Windows Server
Once the certificate and key are exported from Apache and converted to PFX, the next step is securely transferring this file to the Windows server.
Here are the best practices for securely transferring the PFX file:
- Use SFTP: The most secure method is to use SFTP (Secure FTP) to transfer the file over an encrypted connection. Ensure SFTP access is configured correctly on both servers.
- Use Secure Copy: The scp command can copy the file securely between servers. Like SFTP, it transmits the data encrypted.
- Use Encrypted Drives: Copy the file to encrypted external media and physically move it to the Windows server. Enable drive encryption on both servers.
- Use Password-Protected Archives: Compress the PFX into a zip or rar archive protected with a strong password. Transfer the archive securely.
- Do Not Email Unencrypted: Do not email the unencrypted PFX file, as email is not secure. Do not send encrypted email attachments.
- Verify File Integrity: After transfer, confirm that the PFX file’s fingerprint or checksum matches on both servers to ensure integrity.
Proper security measures during file transfer are vital to prevent the private key from being compromised. Following best practices minimizes risk.
Step 4: Import the PFX File into the Windows Server
Once the PFX file is securely transferred to the Windows server, it can be imported in a few steps:
- Open the Microsoft Management Console (MMC) and add the Certificates snap-in to manage certificates on the local computer.
- Right-click the Certificates—Local Computer tree and select All Tasks > Import to launch the certificate import wizard.
- Import the PFX file. Specify the file’s location and enter the passphrase created when initially exporting the certificate and key.
- To confirm the import was successful, ensure the certificate appears under Certificates—Local Computer > Personal > Certificates folder.
- After verifying the import, close the MMC console. The certificate and key are now installed on the Windows server.
With the certificate imported, the next step is to configure HTTPS bindings in IIS to assign it to the appropriate website.
Step 5: Configure SSL Bindings in IIS for the Certificate
The newly imported SSL certificate must be properly bound to the site within Internet Information Services (IIS) for it to secure a website.
Here are the steps to add HTTPS bindings with the imported certificate:
- Open IIS Manager on the Windows server and navigate to the desired website under Sites in the tree.
- Under Actions in the right pane, click Bindings to open the website’s bindings.
- Click Add and select https from the Type dropdown. Choose the imported certificate under the SSL certificate.
- Optionally specify the hostname and port, then click OK to add the HTTPS binding.
- Confirm the site’s bindings now include the imported certificate with HTTPS enabled.
- Restart the website within IIS so the changes take full effect.
The certificate should now show appropriately enabled for the website within IIS. Traffic will be encrypted once DNS records are updated to point traffic to the Windows server.
Step 6: Update DNS Records to Point to the Windows Server
With the certificate imported into the Windows server and assigned to the website in IIS, the final main step is updating DNS records.
- On the DNS server or service managing DNS for the domain, modify the website’s A/AAAA record to point to the Windows server’s IP address.
- If using a load balancer, update it to send traffic to the Windows server instead of the Apache server.
- Propagation of DNS changes can take up to 48 hours. Accelerate by lowering TTL before changing records.
The SSL certificate will be presented by directing traffic to the Windows server and providing encryption without issues or certificate warnings.
Preserve the Apache server’s DNS records during testing if you need to fail temporarily. Only remove old records after completing testing.
Step 7: Test the SSL Certificate and HTTPS on Windows
Before entirely replacing the old Apache server, thoroughly test the certificate and HTTPS on Windows:
- Access the website using HTTPS from various locations and verify no certificate errors are displayed.
- Confirm the correct certificate information displays. Ensure it matches what is displayed on Apache.
- Use online SSL checkers like the one at SSL Labs to analyze the configuration and test for issues.
- Test on multiple browsers and devices to check for problems. Pay extra attention to mobile.
- Validate site performance under HTTPS, ensuring it is satisfactory with no bottlenecks.
- Confirm that secure pages, such as login or protected content, work properly.
Thorough testing helps identify and resolve potential issues with the certificate or HTTPS before decommissioning old infrastructure.
Step 8: Decommission the Certificate and HTTPS on the Apache Server
After successfully validating the migrated SSL certificate on Windows, the last step is cleaning up the old Apache server:
- Revoke the certificate if a certificate authority publicly signed it. This prevents continued use if compromised.
- Remove HTTPS bindings for the certificate from any websites still on Apache.
- Delete the certificate and key files from the disk.
- As mentioned previously, update DNS to point traffic away from Apache permanently.
- Disable and uninstall any unnecessary OpenSSL, certificate authority, or related modules on Apache.
Following decommissioning best practices ensures old certificates and keys are kept caught up, creating security risks or liability. They also prevent overlap that can cause issues.
Final Thoughts
Migrating SSL certificates from Apache to Windows servers involves exporting, securely transferring, importing, and adequately configuring certificates and keys on the new system. Careful attention to detail at each step helps ensure a smooth transition.
Thorough testing and decommissioning of old infrastructure prevent lingering issues. Following best practices for security, performance, and compatibility also reduces potential headaches.
While the process involves coordination and effort, migrating certificates between servers can be straightforward with good planning. The benefits of updated encryption and infrastructure are worth the work.
Frequently Asked Questions About Migrating SSL Certificates from Apache to Windows
Here are some common questions regarding migrating SSL certificates from Apache to Windows servers:
What are the benefits of migrating certificates to Windows?
Some top benefits include improving encryption support in newer versions of Windows, easier centralized management using tools like PowerShell, closer integration with applications like Microsoft IIS, and consolidating multiple legacy systems.
Can I use the same private key when migrating my certificate?
The same private key paired with the SSL certificate can be exported from Apache and imported into Windows. The keys are not tied to a particular server platform.
Do I need to purchase a new SSL certificate for Windows?
No, typically. You can migrate an existing SSL certificate as long as it and its private key are exportable from the Apache server. The same certificate should work fine on Windows.
Can I migrate multiple certificates together?
It is not recommended to export multiple certificates into one combined PFX file. It is best practice to migrate one certificate at a time, following the steps outlined above.
How long should I run Apache and Windows in parallel during migration?
It’s recommended that both environments be run in parallel for at least 1-2 weeks. This provides sufficient testing and rollback time if issues emerge after launching Windows into production.
Do I need to update SAN entries when migrating to a new server?
If the Windows server has hostnames or IPs different from Apache, you may need to update the Subject Alternative Names (SAN) list after importing the certificate. For more information, check the certificate guidelines from your issuer.
Can I migrate my SSL certificate to the cloud instead?
Yes, most cloud hosting providers like AWS and Azure have tools to help you migrate or re-issue existing certificates. The process may differ from the steps outlined in this guide.
Priya Mervana
Verified Web Security Experts
Priya Mervana is working at SSLInsights.com as a web security expert with over 10 years of experience writing about encryption, SSL certificates, and online privacy. She aims to make complex security topics easily understandable for everyday internet users.
