diff --git a/backend/remote/backend_apply_test.go b/backend/remote/backend_apply_test.go
index 8a419a573..355f1c506 100644
--- a/backend/remote/backend_apply_test.go
+++ b/backend/remote/backend_apply_test.go
@@ -1151,6 +1151,7 @@ func TestRemote_applyPolicySoftFail(t *testing.T) {
 		"approve":  "yes",
 	})
 
+	op.AutoApprove = false
 	op.UIIn = input
 	op.UIOut = b.CLI
 	op.Workspace = backend.DefaultStateName
@@ -1187,16 +1188,14 @@ func TestRemote_applyPolicySoftFail(t *testing.T) {
 	}
 }
 
-func TestRemote_applyPolicySoftFailAutoApprove(t *testing.T) {
+func TestRemote_applyPolicySoftFailAutoApproveSuccess(t *testing.T) {
 	b, bCleanup := testBackendDefault(t)
 	defer bCleanup()
 
 	op, configCleanup, done := testOperationApply(t, "./testdata/apply-policy-soft-failed")
 	defer configCleanup()
 
-	input := testInput(t, map[string]string{
-		"override": "override",
-	})
+	input := testInput(t, map[string]string{})
 
 	op.AutoApprove = true
 	op.UIIn = input
@@ -1210,34 +1209,33 @@ func TestRemote_applyPolicySoftFailAutoApprove(t *testing.T) {
 
 	<-run.Done()
 	viewOutput := done(t)
-	if run.Result == backend.OperationSuccess {
-		t.Fatal("expected apply operation to fail")
-	}
-	if !run.PlanEmpty {
-		t.Fatalf("expected plan to be empty")
+	if run.Result != backend.OperationSuccess {
+		t.Fatal("expected apply operation to success due to auto-approve")
 	}
 
-	if len(input.answers) != 1 {
-		t.Fatalf("expected an unused answers, got: %v", input.answers)
+	if run.PlanEmpty {
+		t.Fatalf("expected plan to not be empty, plan opertion completed without error")
+	}
+
+	if len(input.answers) != 0 {
+		t.Fatalf("expected no answers, got: %v", input.answers)
 	}
 
 	errOutput := viewOutput.Stderr()
-	if !strings.Contains(errOutput, "soft failed") {
-		t.Fatalf("expected a policy check error, got: %v", errOutput)
+	if strings.Contains(errOutput, "soft failed") {
+		t.Fatalf("expected no policy check errors, instead got: %v", errOutput)
 	}
 
 	output := b.CLI.(*cli.MockUi).OutputWriter.String()
-	if !strings.Contains(output, "Running apply in the remote backend") {
-		t.Fatalf("expected remote backend header in output: %s", output)
-	}
-	if !strings.Contains(output, "1 to add, 0 to change, 0 to destroy") {
-		t.Fatalf("expected plan summery in output: %s", output)
-	}
 	if !strings.Contains(output, "Sentinel Result: false") {
-		t.Fatalf("expected policy check result in output: %s", output)
+		t.Fatalf("expected policy check to be false, insead got: %s", output)
 	}
-	if strings.Contains(output, "1 added, 0 changed, 0 destroyed") {
-		t.Fatalf("unexpected apply summery in output: %s", output)
+	if !strings.Contains(output, "Apply complete!") {
+		t.Fatalf("expected apply to be complete, instead got: %s", output)
+	}
+
+	if !strings.Contains(output, "Resources: 1 added, 0 changed, 0 destroyed") {
+		t.Fatalf("expected resources, instead got: %s", output)
 	}
 }
 
diff --git a/backend/remote/backend_common.go b/backend/remote/backend_common.go
index fb390acad..7346324ce 100644
--- a/backend/remote/backend_common.go
+++ b/backend/remote/backend_common.go
@@ -414,34 +414,45 @@ func (b *Remote) checkPolicy(stopCtx, cancelCtx context.Context, op *backend.Ope
 		case tfe.PolicyHardFailed:
 			return fmt.Errorf(msgPrefix + " hard failed.")
 		case tfe.PolicySoftFailed:
+			runUrl := fmt.Sprintf(runHeader, b.hostname, b.organization, op.Workspace, r.ID)
+
 			if op.Type == backend.OperationTypePlan || op.UIOut == nil || op.UIIn == nil ||
-				op.AutoApprove || !pc.Actions.IsOverridable || !pc.Permissions.CanOverride {
-				return fmt.Errorf(msgPrefix + " soft failed.")
+				!pc.Actions.IsOverridable || !pc.Permissions.CanOverride {
+				return fmt.Errorf(msgPrefix + " soft failed.\n" + runUrl)
+			}
+
+			if op.AutoApprove {
+				if _, err = b.client.PolicyChecks.Override(stopCtx, pc.ID); err != nil {
+					return generalError(fmt.Sprintf("Failed to override policy check.\n%s", runUrl), err)
+				}
+			} else {
+				opts := &terraform.InputOpts{
+					Id:          "override",
+					Query:       "\nDo you want to override the soft failed policy check?",
+					Description: "Only 'override' will be accepted to override.",
+				}
+				err = b.confirm(stopCtx, op, opts, r, "override")
+				if err != nil && err != errRunOverridden {
+					return fmt.Errorf(
+						fmt.Sprintf("Failed to override: %s\n%s\n", err.Error(), runUrl),
+					)
+				}
+
+				if err != errRunOverridden {
+					if _, err = b.client.PolicyChecks.Override(stopCtx, pc.ID); err != nil {
+						return generalError(fmt.Sprintf("Failed to override policy check.\n%s", runUrl), err)
+					}
+				} else {
+					b.CLI.Output(fmt.Sprintf("The run needs to be manually overridden or discarded.\n%s\n", runUrl))
+				}
+			}
+
+			if b.CLI != nil {
+				b.CLI.Output("------------------------------------------------------------------------")
 			}
 		default:
 			return fmt.Errorf("Unknown or unexpected policy state: %s", pc.Status)
 		}
-
-		opts := &terraform.InputOpts{
-			Id:          "override",
-			Query:       "\nDo you want to override the soft failed policy check?",
-			Description: "Only 'override' will be accepted to override.",
-		}
-
-		err = b.confirm(stopCtx, op, opts, r, "override")
-		if err != nil && err != errRunOverridden {
-			return err
-		}
-
-		if err != errRunOverridden {
-			if _, err = b.client.PolicyChecks.Override(stopCtx, pc.ID); err != nil {
-				return generalError("Failed to override policy check", err)
-			}
-		}
-
-		if b.CLI != nil {
-			b.CLI.Output("------------------------------------------------------------------------")
-		}
 	}
 
 	return nil