diff --git a/controllers/ipc_config_handlers.go b/controllers/ipc_config_handlers.go
index c3900ab8ec..1f355830bc 100644
--- a/controllers/ipc_config_handlers.go
+++ b/controllers/ipc_config_handlers.go
@@ -893,7 +893,7 @@ func validateAddressChanges(ipc *ipcv1.IPConfig) error {
 			v4,
 			ipc.Status.IPv4,
 		); err != nil {
-			return err
+			return fmt.Errorf("failed to validate IPv4 address changes: %w", err)
 		}
 	}
 
@@ -903,7 +903,7 @@ func validateAddressChanges(ipc *ipcv1.IPConfig) error {
 			v6,
 			ipc.Status.IPv6,
 		); err != nil {
-			return err
+			return fmt.Errorf("failed to validate IPv6 address changes: %w", err)
 		}
 	}
 
diff --git a/controllers/ipc_idle_handlers.go b/controllers/ipc_idle_handlers.go
index 25dfc5e2b0..d9902505e7 100644
--- a/controllers/ipc_idle_handlers.go
+++ b/controllers/ipc_idle_handlers.go
@@ -204,7 +204,7 @@ func (h *IPCIdleStageHandler) cleanuoUnbootedStateroots(logger logr.Logger) erro
 	}
 
 	if err := removeBootDirsByStaterootPrefixes(logger, h.ChrootOps, staterootsToRemove); err != nil {
-		return err
+		return fmt.Errorf("failed to remove boot dirs by stateroot prefixes: %w", err)
 	}
 
 	if err := CleanupUnbootedStateroots(logger, h.ChrootOps, h.OstreeClient, h.RPMOstreeClient); err != nil {
diff --git a/controllers/ipc_rollback_handlers.go b/controllers/ipc_rollback_handlers.go
index f5dfd60e7b..79f341980c 100644
--- a/controllers/ipc_rollback_handlers.go
+++ b/controllers/ipc_rollback_handlers.go
@@ -305,7 +305,7 @@ func (r *IPCRollbackTwoPhaseHandler) scheduleIPConfigRollback(
 
 func (h *IPCRollbackStageHandler) validateRollbackStart() error {
 	if err := h.validateUnbootedStaterootAvailable(); err != nil {
-		return err
+		return fmt.Errorf("failed to validate unbooted stateroot availability: %w", err)
 	}
 
 	return nil
diff --git a/internal/clusterconfig/clusterconfig.go b/internal/clusterconfig/clusterconfig.go
index 122b0d2590..10b62cfec6 100644
--- a/internal/clusterconfig/clusterconfig.go
+++ b/internal/clusterconfig/clusterconfig.go
@@ -69,22 +69,22 @@ func (r *UpgradeClusterConfigGather) FetchClusterConfig(ctx context.Context, ost
 
 	clusterConfigPath, err := r.configDir(ostreeVarDir)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get cluster config directory: %w", err)
 	}
 	manifestsDir := filepath.Join(clusterConfigPath, ManifestDir)
 
 	if err := r.fetchIDMS(ctx, manifestsDir); err != nil {
-		return err
+		return fmt.Errorf("failed to fetch IDMS: %w", err)
 	}
 
 	if err := r.fetchClusterInfo(ctx, clusterConfigPath); err != nil {
-		return err
+		return fmt.Errorf("failed to fetch cluster info: %w", err)
 	}
 	if err := r.fetchICSPs(ctx, manifestsDir); err != nil {
-		return err
+		return fmt.Errorf("failed to fetch ICSPs: %w", err)
 	}
 	if err := r.fetchNetworkConfig(ostreeVarDir); err != nil {
-		return err
+		return fmt.Errorf("failed to fetch network config: %w", err)
 	}
 
 	r.Log.Info("Successfully fetched cluster configuration")
@@ -350,42 +350,42 @@ func (r *UpgradeClusterConfigGather) fetchClusterInfo(ctx context.Context, clust
 
 	infraID, err := r.getInfraID(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get infra ID: %w", err)
 	}
 
 	pullSecret, err := r.getPullSecret(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get pull secret: %w", err)
 	}
 
 	kubeadminPasswordHash, err := r.GetKubeadminPasswordHash(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get kubeadmin password hash: %w", err)
 	}
 
 	serverSSHKeys, err := r.GetServerSSHKeys(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get server SSH keys: %w", err)
 	}
 
 	proxy, statusProxy, err := r.GetProxy(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get proxy config: %w", err)
 	}
 
 	additionalTrustBundle, err := r.GetAdditionalTrustBundle(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get additional trust bundle: %w", err)
 	}
 
 	installConfig, err := r.GetInstallConfig(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get install config: %w", err)
 	}
 
 	chronyConfig, err := r.getChronyConfig()
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get chrony config: %w", err)
 	}
 
 	seedReconfiguration := SeedReconfigurationFromClusterInfo(clusterInfo, seedReconfigurationKubeconfigRetention,
@@ -414,7 +414,7 @@ func (r *UpgradeClusterConfigGather) fetchIDMS(ctx context.Context, manifestsDir
 	r.Log.Info("Fetching IDMS")
 	idms, err := r.getIDMSs(ctx)
 	if err != nil {
-		return fmt.Errorf("failed to fetch IDMS")
+		return fmt.Errorf("failed to fetch IDMS: %w", err)
 	}
 
 	if len(idms.Items) < 1 {
@@ -514,7 +514,7 @@ func (r *UpgradeClusterConfigGather) fetchICSPs(ctx context.Context, manifestsDi
 		}
 		typeMeta, err := r.typeMetaForObject(&icp) //nolint:gosec
 		if err != nil {
-			return err
+			return fmt.Errorf("failed to get type meta for ICSP %s: %w", icp.Name, err)
 		}
 		obj.TypeMeta = *typeMeta
 		obj.Labels = icp.Labels
@@ -523,7 +523,7 @@ func (r *UpgradeClusterConfigGather) fetchICSPs(ctx context.Context, manifestsDi
 	}
 	typeMeta, err := r.typeMetaForObject(iscpsList)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to get type meta for ICSP list: %w", err)
 	}
 	iscpsList.TypeMeta = *typeMeta
 
diff --git a/internal/clusterconfig/lvmconfig.go b/internal/clusterconfig/lvmconfig.go
index 245375b832..74ca00f798 100644
--- a/internal/clusterconfig/lvmconfig.go
+++ b/internal/clusterconfig/lvmconfig.go
@@ -45,12 +45,12 @@ func (r *UpgradeClusterConfigGather) FetchLvmConfig(ctx context.Context, ostreeD
 	}
 
 	if err := r.fetchLvmDevices(lvmConfigPath); err != nil {
-		return err
+		return fmt.Errorf("failed to fetch LVM devices: %w", err)
 	}
 
 	manifestsDir := filepath.Join(ostreeDir, common.OptOpenshift, common.ClusterConfigDir, ManifestDir)
 	if err := r.fetchLocalVolumes(ctx, manifestsDir); err != nil {
-		return err
+		return fmt.Errorf("failed to fetch local volumes: %w", err)
 	}
 
 	r.Log.Info("Successfully fetched lvm configuration")