Troubleshooting the Hybrid Configuration Wizard: How to Resolve Connection Issues with Office 365

Published On - November 16, 2024 by Armaan | Reading Time: 4 minutes

“Connecting to remote server failed with the following error message: Connecting to remote server outlook.office365.com failed with the following error message: The server certificate on the destination computer (outlook.office365.com:443) has the following errors: Encountered an internal error in the SSL library. For more information, see the about_Remote_Troubleshooting Help topic.”

Have you ever received any error message like this while running “Hybrid Configuration Wizard (HCW)”? This error generally happens when you try to set up a hybrid system between your on-premises Exchange Server and Office 365 and HCW won’t connect. Many organizations perform this task when moving to the cloud. However, if the O365 Hybrid Configuration Wizard fails to connect, it stops and halts everything. So, here is a guide to help you troubleshoot the issue. We will ensure you establish a smooth connection between the local Exchange Server and Office 365. You can consider using the EDB Data Migration Tool for hassle-free migration of Exchange files to Office 365.

What is the Hybrid Configuration Wizard?

HWC is a tool that connects an on-premises Exchange Server to Office 365 (Exchange Online). This connection allows organizations to store some mailboxes on-premises while using Office 365 services, Thus, providing flexibility during a gradual migration. Exchange hybrid configuration wizard involves some major steps. Firstly, you need to enter credentials for both servers (Local Exchange Server), and then the tool will verify the connectivity. Afterward, it configures hybrid components.

However, sometimes it might encounter the Office 365 Hybrid Configuration Wizard connecting to remote server failed error. Consequently, it disrupts the whole setup. Such an error can occur due to several reasons, some of them are:

• Network connectivity issues or firewall restrictions.
• Outdated protocols (HCW requires TLS 1.2 to connect with Office 365).
• Mismatched or improperly configured certificates.

Now, let us know how to troubleshoot this error using the easiest and most reliable method.

Troubleshoot Connectivity Issue of Hybrid Configuration Wizard Step-by-Step

Besides, there can be many others causing the issue ‘HCW is not able to connect to the Office 365 tenant’. Therefore, we will begin to resolve this issue by basic measures first. Do the following before proceeding to the actual procedure:

• Firstly, you must check for stable network connectivity.
• Go through the firewall settings. Sometimes, they might block connections.
• Close the Hybrid Configuration Wizard and restart it. If problems persist check for certificate configuration.

Is the connectivity problem resolved? If not yet, possibly issues with TLS support on the local machine are the reason. Let us know in detail.

Confirm TLS 1.2 Support on Your System

It’s important to enable TLS 1.2, to connect HWC to Office 365. If somehow, this protocol is missing, the Hybrid Configuration Wizard won’t connect. Here’s a breakdown of TLS 1.2 support across different Windows OS versions:

If you are using any of the Windows OS mentioned above and TLS 1.2 is disabled, upgrade to the latest operating system. We have explained ways to enable TLS 2.1 on your system (where TLS 2.1 is not enabled). Read further and follow the steps below to enable it.

How to Enable TLS 1.2 on Windows Servers for Hybrid Configuration Wizard?

1. For Older OS versions like Windows Server 2008 R2, Windows 7, or Windows Server 2012, install KB3140245.
2. Now, confirm that the TLS 1.2 protocol is set as the default protocol in WinHTTP.
3. Once the update is installed, modify the Windows registry to enable TLS 1.2.

For 32-bit OS
HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp

For 64-bit OS
HKEY_LOCAL_MACHINE\SOFTWARE\Wow6432Node\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp

4. If you don’t see the DefaultSecureProtocols key, create a new DWORD key with this name. Set its value to 0x00000800 to enable TLS 1.2. If you want to enable TLS 1.0, 1.1, and 1.2 together, set the value to 0x00000A80.

Hence, TLS 1.2 is enabled at at WinHTTP level. Somehow, if the issue persists, user need to enable it in Internet Settings (from the operating system level).

Enable TLS 1.2 Protocol in Internet Settings

This can be done by editing the inetcpl.cpl. Follow the procedure below:

1. Search inetcpl.cpl in the Windows Search tab and open the Internet Options.
2. Next, click on the Advanced option.
3. Find the Use TLS 1.2 option, and tick the Use TLS 1.2 checkbox.
4. At last, click OK to save changes.
5. Later, restart the Server to apply the changes.

Finally, this configuration should allow connecting the Office 365 Hybrid Configuration Wizard successfully.

Alternative Solution: Bypass Exchange Hybrid Configuration Wizard Issue

There is possibility that the troubleshooting O365 Hybrid Configuration may not resolve. Manual process involves complex procedure that many users find it difficult. If that is so, you can consider this professional solution. Use Regain EDB to PST Converter that simplifies the migration process. It is a specialized tool to transfer all mailboxes, archives, and shared folders directly to Office 365 or Exchange Server. Moreover, the tool is free from any complex setups. You can also take backup of your EDB files into multiple formats like PST, MBOX, MSG, HTML, PDF, etc. Better you run the free tool to evaluate its working before buying it.

Free Download100% Secure Buy NowPrice: $89

Follow the procedure given below to run the tool:

1. Install the EDB File Converter and run it on your system.
2. Select and add Exchange Server files to convert/migrate.
3. Once scanning of added files are over preview mailbox data.
4. Next, click on Cloud Migration at the top to export data.
5. Choose the Office 365/Exchange Server option as destination.
6. Login to your destination account and proceed to migration.

Hence, no more hassle of download the hybrid configuration wizard, technical errors and protocol settings.

Conclusion

The process to set up a hybrid Exchange migration with the Hybrid Configuration Wizard is full of hassle and complexity. However, knowing the step-by-step process and troubleshooting tips can be helpful for tech savvys. Whatever has caused the issue, these steps might help you restoring connectivity with O365. On the other hand, we have shared a more reliable migration method to bypass this complexity of manual procedure. Use the suggested software to ensure a smooth migration experience.