diff --git a/cmd/bundle/generate/dashboard.go b/cmd/bundle/generate/dashboard.go
index 416ca64d1b..e139c4b1c7 100644
--- a/cmd/bundle/generate/dashboard.go
+++ b/cmd/bundle/generate/dashboard.go
@@ -3,6 +3,7 @@ package generate
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"os"
 	"path"
@@ -14,6 +15,7 @@ import (
 	"github.com/databricks/cli/bundle/config/generate"
 	"github.com/databricks/cli/bundle/deploy/terraform"
 	"github.com/databricks/cli/bundle/phases"
+	"github.com/databricks/cli/bundle/render"
 	"github.com/databricks/cli/cmd/root"
 	"github.com/databricks/cli/libs/diag"
 	"github.com/databricks/cli/libs/dyn"
@@ -64,8 +66,24 @@ func (d *dashboard) resolveFromPath(ctx context.Context, b *bundle.Bundle) (stri
 	obj, err := w.Workspace.GetStatusByPath(ctx, d.dashboardPath)
 	if err != nil {
 		if apierr.IsMissing(err) {
-			return "", diag.Errorf("dashboard at path %q not found", d.dashboardPath)
+			return "", diag.Errorf("dashboard %q not found", path.Base(d.dashboardPath))
 		}
+
+		// Emit a more descriptive error message for legacy dashboards.
+		if errors.Is(err, apierr.ErrBadRequest) && strings.HasPrefix(err.Error(), "dbsqlDashboard ") {
+			return "", diag.Diagnostics{
+				{
+					Severity: diag.Error,
+					Summary:  fmt.Sprintf("dashboard %q is a legacy dashboard", path.Base(d.dashboardPath)),
+					Detail: "" +
+						"Databricks Asset Bundles work exclusively with AI/BI dashboards.\n" +
+						"\n" +
+						"Instructions on how to convert a legacy dashboard to an AI/BI dashboard\n" +
+						"can be found at: https://docs.databricks.com/en/dashboards/clone-legacy-to-aibi.html.",
+				},
+			}
+		}
+
 		return "", diag.FromErr(err)
 	}
 
@@ -184,7 +202,7 @@ func (d *dashboard) saveConfiguration(ctx context.Context, b *bundle.Bundle, das
 	}
 
 	// Save the configuration to the resource directory.
-	resourcePath := filepath.Join(d.resourceDir, fmt.Sprintf("%s.yml", key))
+	resourcePath := filepath.Join(d.resourceDir, fmt.Sprintf("%s.dashboard.yml", key))
 	saver := yamlsaver.NewSaverWithStyle(map[string]yaml.Style{
 		"display_name": yaml.DoubleQuotedStyle,
 	})
@@ -347,7 +365,17 @@ func (d *dashboard) RunE(cmd *cobra.Command, args []string) error {
 		diags = d.runForExisting(ctx, b)
 	}
 
-	return diags.Error()
+	renderOpts := render.RenderOptions{RenderSummaryTable: false}
+	err := render.RenderDiagnostics(cmd.OutOrStdout(), b, diags, renderOpts)
+	if err != nil {
+		return fmt.Errorf("failed to render output: %w", err)
+	}
+
+	if diags.HasError() {
+		return root.ErrAlreadyPrinted
+	}
+
+	return nil
 }
 
 func NewGenerateDashboardCommand() *cobra.Command {
diff --git a/cmd/bundle/generate/dashboard_test.go b/cmd/bundle/generate/dashboard_test.go
index eb8347795a..8df6650795 100644
--- a/cmd/bundle/generate/dashboard_test.go
+++ b/cmd/bundle/generate/dashboard_test.go
@@ -1 +1,43 @@
 package generate
+
+import (
+	"context"
+	"testing"
+
+	"github.com/databricks/cli/bundle"
+	"github.com/databricks/databricks-sdk-go/apierr"
+	"github.com/databricks/databricks-sdk-go/experimental/mocks"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/mock"
+	"github.com/stretchr/testify/require"
+)
+
+func TestDashboard_ErrorOnLegacyDashboard(t *testing.T) {
+	// Response to a GetStatus request on a path pointing to a legacy dashboard.
+	//
+	// < HTTP/2.0 400 Bad Request
+	// < {
+	// <   "error_code": "BAD_REQUEST",
+	// <   "message": "dbsqlDashboard is not user-facing."
+	// < }
+
+	d := dashboard{
+		dashboardPath: "/path/to/legacy dashboard",
+	}
+
+	m := mocks.NewMockWorkspaceClient(t)
+	w := m.GetMockWorkspaceAPI()
+	w.On("GetStatusByPath", mock.Anything, "/path/to/legacy dashboard").Return(nil, &apierr.APIError{
+		StatusCode: 400,
+		ErrorCode:  "BAD_REQUEST",
+		Message:    "dbsqlDashboard is not user-facing.",
+	})
+
+	ctx := context.Background()
+	b := &bundle.Bundle{}
+	b.SetWorkpaceClient(m.WorkspaceClient)
+
+	_, diags := d.resolveID(ctx, b)
+	require.Len(t, diags, 1)
+	assert.Equal(t, diags[0].Summary, "dashboard \"legacy dashboard\" is a legacy dashboard")
+}