diff --git a/internal/monitoring/monitor_polling.go b/internal/monitoring/monitor_polling.go
index b609347..a44c687 100644
--- a/internal/monitoring/monitor_polling.go
+++ b/internal/monitoring/monitor_polling.go
@@ -513,6 +513,8 @@ func (m *Monitor) pollVMsWithNodes(ctx context.Context, instanceName string, cli
 								Str("error", errStr).
 								Msg("Failed to get VM filesystem info from guest agent")
 
+							// Classify the error type for better user messaging
+							// Order matters: check most specific patterns first
 							if strings.Contains(errStr, "QEMU guest agent is not running") {
 								diskStatusReason = "agent-not-running"
 								log.Info().
@@ -520,10 +522,36 @@ func (m *Monitor) pollVMsWithNodes(ctx context.Context, instanceName string, cli
 									Str("vm", vm.Name).
 									Int("vmid", vm.VMID).
 									Msg("Guest agent enabled in VM config but not running inside guest OS. Install and start qemu-guest-agent in the VM")
-							} else if strings.Contains(err.Error(), "timeout") {
+							} else if strings.Contains(errStr, "timeout") {
 								diskStatusReason = "agent-timeout"
-							} else if strings.Contains(err.Error(), "permission denied") || strings.Contains(err.Error(), "not allowed") {
+							} else if strings.Contains(errStr, "500") && (strings.Contains(errStr, "not running") || strings.Contains(errStr, "not available")) {
+								// Proxmox API error 500 with "not running"/"not available" indicates guest agent issue, not permissions
+								// This commonly happens when guest agent is not installed or not running
+								diskStatusReason = "agent-not-running"
+								log.Info().
+									Str("instance", instanceName).
+									Str("vm", vm.Name).
+									Int("vmid", vm.VMID).
+									Msg("Guest agent communication failed (API error 500). Install and start qemu-guest-agent in the VM")
+							} else if (strings.Contains(errStr, "403") || strings.Contains(errStr, "401")) &&
+								(strings.Contains(strings.ToLower(errStr), "permission") || strings.Contains(strings.ToLower(errStr), "forbidden") || strings.Contains(strings.ToLower(errStr), "not allowed")) {
+								// Only treat as permission-denied if we get explicit auth/permission error codes (401/403)
+								// This distinguishes actual permission issues from guest agent unavailability
 								diskStatusReason = "permission-denied"
+								log.Warn().
+									Str("instance", instanceName).
+									Str("vm", vm.Name).
+									Int("vmid", vm.VMID).
+									Msg("Permission denied accessing guest agent. Verify Pulse user has VM.Monitor (PVE 8) or VM.Audit+VM.GuestAgent.Audit (PVE 9) permissions")
+							} else if strings.Contains(errStr, "500") {
+								// Generic 500 error without clear indicators - likely agent unavailable
+								// Refs #596: Proxmox returns 500 errors when guest agent isn't installed/running
+								diskStatusReason = "agent-not-running"
+								log.Info().
+									Str("instance", instanceName).
+									Str("vm", vm.Name).
+									Int("vmid", vm.VMID).
+									Msg("Failed to communicate with guest agent (API error 500). This usually means qemu-guest-agent is not installed or not running in the VM")
 							} else {
 								diskStatusReason = "agent-error"
 							}