diff --git a/.changelog/3602.txt b/.changelog/3602.txt
new file mode 100644
index 00000000000..d723d7290e2
--- /dev/null
+++ b/.changelog/3602.txt
@@ -0,0 +1,4 @@
+```release-note:bug
+cli: `deployment destroy` will now attempt to destroy any known resources for failed
+deployments. Previously, `destroy` would skip unsuccessful deployments.
+```
\ No newline at end of file
diff --git a/internal/cli/deployment_destroy.go b/internal/cli/deployment_destroy.go
index 4c08b0aa2fa..dd35b0b0462 100644
--- a/internal/cli/deployment_destroy.go
+++ b/internal/cli/deployment_destroy.go
@@ -2,6 +2,7 @@ package cli
 
 import (
 	"context"
+	"errors"
 	"strconv"
 
 	"github.com/posener/complete"
@@ -60,10 +61,12 @@ func (c *DeploymentDestroyCommand) Run(args []string) int {
 
 		// Destroy each deployment
 		c.ui.Output("%d deployments will be destroyed.", len(deployments), terminal.WithHeaderStyle())
+		var destroymentErrors []error
 		for _, deployment := range deployments {
 			// Can't destroy a deployment that was not successful
 			if deployment.Status.GetState() != pb.Status_SUCCESS {
-				continue
+				c.ui.Output("Deployment %d was not successful - destroy may not completely destroy "+
+					"all resources", deployment.Sequence, terminal.WithWarningStyle())
 			}
 
 			// Get our app client
@@ -75,10 +78,13 @@ func (c *DeploymentDestroyCommand) Run(args []string) int {
 					Deployment: deployment,
 				},
 			}); err != nil {
-				c.ui.Output("Error destroying the deployment: %s", err.Error(), terminal.WithErrorStyle())
-				return ErrSentinel
+				c.ui.Output("Error destroying deployment %d: %s", deployment.Sequence, err.Error(), terminal.WithErrorStyle())
+				destroymentErrors = append(destroymentErrors, err)
 			}
 		}
+		if len(destroymentErrors) > 0 {
+			return errors.New("one or more deployments failed to be destroyed")
+		}
 		return nil
 	})
 	if err != nil {