Troubleshoot problems with vSphere Lifecycle Manager proxy configuration

Products

• VMware vCenter Server

Issue/Introduction

Users may experience difficulties with vSphere Lifecycle Manager failing to download updates. This issue commonly manifests as:
- Lifecycle Manager showing download sources as "Not Connected"
- Failed download tasks with messages indicating inaccessible depots or patch data
- Inability to sync updates or download patch definitions

Environment

- VMware vCenter Server 7.0.x and newer
- Environments using proxy servers for internet access

Cause

This issue typically occurs due to incorrect proxy configuration or network connectivity problems between the vCenter Server and the update sources. See Configuring the vSphere Lifecycle Manager Download Sources 

Also, using HTTPS for the proxy server connection in vSphere Lifecycle Manager is not supported. This is due to limitations in the Python "requests" module used by VLCM to validate online depots, which does not properly handle HTTPS proxy connections. You must use HTTP for the proxy server connection, even when the final target URLs use HTTPS. This means setting the proxy URL to "http://" in the vCenter configuration, regardless of whether the proxy server itself supports HTTPS connections.

Resolution

Follow these steps to troubleshoot and resolve the issue:

1. Verify proxy settings:
   a. Access the vCenter Server Appliance Management Interface (VAMI) at https://<vcenter-ip>:5480
   b. Navigate to Networking and review the current proxy settings

2. Check the proxy configuration file:
   a. SSH into the vCenter Server Appliance
   b. Run: cat /etc/sysconfig/proxy
   c. Ensure HTTP_PROXY and HTTPS_PROXY entries don't have leading slashes

3. Modify proxy settings if necessary:
   a. SSH into the vCenter Server Appliance
   b. Edit the proxy configuration file: vi /etc/sysconfig/proxy
   c. Ensure that you are using HTTP for the proxy server connection, even if the proxy server supports HTTPS
   e. Edit the proxy configuration file: vi /etc/sysconfig/proxy
   f. Set both HTTP_PROXY and HTTPS_PROXY to use HTTP, e.g.:
      HTTP_PROXY="http://<your-proxy:port>/"
   HTTPS_PROXY="http://<your-proxy:port>/"
      Note: Use "http://" in these settings even though HTTPS_PROXY is for HTTPS target URLs
   g. Ensure there's no leading slash and add a trailing slash to proxy URLs
   h. Add necessary domains to NO_PROXY, e.g., NO_PROXY="hostupdate.vmware.com, localhost, 127.0.0.1"

4. Test connectivity:
   Run the following commands, replacing <your-proxy:port> with your actual proxy address and port:
   a. curl -I http://hostupdate.vmware.com
   b. curl -I https://hostupdate.vmware.com
   c. HTTP_PROXY="http://<your-proxy:port>/" curl -I http://hostupdate.vmware.com
   d. HTTPS_PROXY="http://<your-proxy:port>/" curl -I https://hostupdate.vmware.com
   Note: In steps c and d, we're using "http://" for the proxy, even when testing HTTPS URLs

5. Reboot the vCenter Server Appliance to apply changes

6. Check Lifecycle Manager download sources:
   a. In vSphere Client, go to Menu > Lifecycle Manager > Settings > Patch Setup
   b. Verify the status of download sources
   c. Manually trigger a download by clicking "CHECK COMPLIANCE" in the Updates tab

7. Perform a manual download test:
   Run the following command, replacing <your-proxy:port> with your actual proxy address and port:
   curl -x http://<your-proxy:port> https://hostupdate.vmware.com/software/VUM/PRODUCTION/addon-main/vmw-depot-index.xml
   This command tests downloading directly from the VMware update server through your proxy, using HTTP for the proxy connection but HTTPS for the target URL.

8. If issues persist, consider using Update Manager Download Service (UMDS)
    See VMware Docs Configuring the vSphere Lifecycle Manager Download Sources

If these steps do not resolve the issue, contact VMware Support for further assistance.

Additional Information

• The limitation regarding HTTPS proxy support affects only the connection to the proxy server itself. The target URLs (e.g., hostupdate.vmware.com) can and should still use HTTPS.
• This configuration allows HTTPS connections to target URLs while using HTTP for the proxy connection itself, maintaining security for the actual update server connections.
• If your security requirements mandate the use of HTTPS for proxy connections, you may need to implement additional security measures at the network level while using HTTP proxy settings for vSphere Lifecycle Manager.
• Ensure your environment meets the network requirements for vSphere Lifecycle Manager as outlined in the vSphere documentation
  See the VMware Ports and Protocols tool​
• If you suspect SSL interception might be causing issues, refer to vSphere Update Manager / Lifecycle Manager fails to download updates due to SSL Interception for additional troubleshooting steps