diff --git a/internal/deployer/operator_olm.go b/internal/deployer/operator_olm.go
index 99fc63f..9428cac 100644
--- a/internal/deployer/operator_olm.go
+++ b/internal/deployer/operator_olm.go
@@ -13,11 +13,12 @@ import (
 )
 
 const (
-	catalogSourceName  = "stackrox-operator-index"
-	subscriptionName   = "stackrox-operator-subscription"
-	operatorGroupName  = "all-namespaces-operator-group"
-	operatorChannel    = "latest"
-	operatorIndexImage = "quay.io/rhacs-eng/stackrox-operator-index"
+	catalogSourceName          = "stackrox-operator-index"
+	subscriptionName           = "stackrox-operator-subscription"
+	operatorGroupName          = "all-namespaces-operator-group"
+	operatorChannel            = "latest"
+	operatorIndexImage         = "quay.io/rhacs-eng/stackrox-operator-index"
+	namespacedSubscriptionName = operatorNamespace + "/" + subscriptionName
 )
 
 // OperatorDeploymentMode represents how the operator is deployed
@@ -65,7 +66,7 @@ func (d *Deployer) deployOperatorViaOLM(ctx context.Context) error {
 	}
 
 	if err := d.waitForOperatorReady(ctx, operatorNamespace, operatorDeploymentName, 300); err != nil {
-		return fmt.Errorf("failed waiting for operator: %w", err)
+		return fmt.Errorf("failed waiting for operator in namespace %s to become ready: %w", operatorNamespace, err)
 	}
 
 	d.logger.Success("🎉 Operator deployed successfully via OLM!")
@@ -226,7 +227,7 @@ func (d *Deployer) createSubscription(ctx context.Context) error {
 		Stdin: bytes.NewReader(yamlData),
 	})
 	if err != nil {
-		return fmt.Errorf("failed to create Subscription: %w", err)
+		return fmt.Errorf("failed to create Subscription %s: %w", namespacedSubscriptionName, err)
 	}
 
 	d.logger.Success("✓ Subscription created")
@@ -253,9 +254,7 @@ func (d *Deployer) waitForAndApproveInstallPlan(ctx context.Context) error {
 	}
 
 	if time.Since(start) >= timeout {
-		// TODO(ROX-34499): some more info on what was wrong would be useful: a dump of the
-		// subscription or at least its name so that the user can investigate
-		return errors.New("timeout waiting for InstallPlan to be created")
+		return fmt.Errorf("timeout waiting for InstallPlan to be created for Subscription %s", namespacedSubscriptionName)
 	}
 
 	// Sanity check:Verify currentCSV matches expected version.
@@ -264,12 +263,12 @@ func (d *Deployer) waitForAndApproveInstallPlan(ctx context.Context) error {
 		Args: []string{"get", "subscription", subscriptionName, "-n", operatorNamespace, "-o", "jsonpath={.status.currentCSV}"},
 	})
 	if err != nil {
-		return fmt.Errorf("failed to get current CSV from subscription: %w", err)
+		return fmt.Errorf("failed to get current CSV from Subscription %s: %w", namespacedSubscriptionName, err)
 	}
 
 	currentCSV := strings.TrimSpace(result.Stdout)
 	if currentCSV != expectedCSV {
-		return fmt.Errorf("subscription progressing to unexpected CSV '%s', expected '%s'", currentCSV, expectedCSV)
+		return fmt.Errorf("detected Subscription %s progressing to unexpected CSV '%s', expected '%s'", namespacedSubscriptionName, currentCSV, expectedCSV)
 	}
 
 	// Get InstallPlan name.
@@ -277,7 +276,7 @@ func (d *Deployer) waitForAndApproveInstallPlan(ctx context.Context) error {
 		Args: []string{"get", "subscription", subscriptionName, "-n", operatorNamespace, "-o", "jsonpath={.status.installPlanRef.name}"},
 	})
 	if err != nil {
-		return fmt.Errorf("failed to get InstallPlan name: %w", err)
+		return fmt.Errorf("failed to get InstallPlan name from Subscription %s: %w", namespacedSubscriptionName, err)
 	}
 
 	installPlanName := strings.TrimSpace(result.Stdout)
@@ -292,7 +291,7 @@ func (d *Deployer) waitForAndApproveInstallPlan(ctx context.Context) error {
 		Args: []string{"patch", "installplan", installPlanName, "-n", operatorNamespace, "--type", "merge", "-p", `{"spec":{"approved":true}}`},
 	})
 	if err != nil {
-		return fmt.Errorf("failed to approve InstallPlan: %w", err)
+		return fmt.Errorf("failed to approve InstallPlan %s for Subscription %s: %w", installPlanName, namespacedSubscriptionName, err)
 	}
 
 	d.logger.Success("✓ InstallPlan approved")
@@ -325,8 +324,7 @@ func (d *Deployer) waitForCSVSuccess(ctx context.Context) error {
 		time.Sleep(5 * time.Second)
 	}
 
-	// TODO(ROX-34499): same as above
-	return fmt.Errorf("timeout waiting for CSV to succeed")
+	return fmt.Errorf("timeout waiting for CSV %s to succeed", csvName)
 }
 
 // detectOperatorDeploymentMode detects how the operator is currently deployed.