On Windows Server 2016, Extend Volume is often greyed out because unallocated space is not directly to the right of the target partition.

If Disk Management cannot extend the volume, first check where the unallocated space is. Qiling Disk Master can move or extend partitions with a preview, which is useful on Windows Server 2016 when a recovery, data, or OEM partition blocks the free space.
Step 1. Open Qiling Disk Master during a maintenance window. Find the target volume by disk number, drive letter, capacity, and file system. Make sure you are working on the correct Server 2016 disk.

Step 2. Right-click the target volume and choose Resize/Move. Drag the border toward the adjacent unallocated space, or enter the new size manually.

Step 3. Check the preview. If the layout is correct, click Proceed. If the system volume is involved, allow the server to restart and finish the operation before Windows loads.
Step 1. Identify the partition between the target volume and the unallocated space. If it stores data, back it up first. If BitLocker is enabled, unlock or suspend protection before changing the layout.
Step 2. Use Resize/Move on the blocking partition and move it to the right side of the disk, so the unallocated space becomes directly adjacent to the target volume.

Step 3. Select the target volume again, extend it into the adjacent unallocated space, review all pending operations, and click Proceed.
Handle the visible symptom first, then protect data before any delete, format, resize, or clone action. If the disk layout is confusing, use a visual tool and confirm the target before you click Proceed.