diff --git a/bundle/config/mutator/process_root_includes.go b/bundle/config/mutator/process_root_includes.go
index ef055674a..454e3a987 100644
--- a/bundle/config/mutator/process_root_includes.go
+++ b/bundle/config/mutator/process_root_includes.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"fmt"
 	"path/filepath"
+	"strings"
 
 	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/bundle/config"
@@ -49,6 +50,12 @@ func (m *processRootIncludes) Apply(ctx context.Context, b *bundle.Bundle) error
 			return err
 		}
 
+		// If the entry is not a glob pattern and no matches found,
+		// return an error because the file defined is not found
+		if len(matches) == 0 && !strings.ContainsAny(entry, "*?[") {
+			return fmt.Errorf("%s defined in 'include' section does not match any files", entry)
+		}
+
 		// Filter matches to ones we haven't seen yet.
 		var includes []string
 		for _, match := range matches {
diff --git a/bundle/config/mutator/process_root_includes_test.go b/bundle/config/mutator/process_root_includes_test.go
index 1e7f6d1a2..c7d00d88b 100644
--- a/bundle/config/mutator/process_root_includes_test.go
+++ b/bundle/config/mutator/process_root_includes_test.go
@@ -108,3 +108,17 @@ func TestProcessRootIncludesRemoveDups(t *testing.T) {
 	require.NoError(t, err)
 	assert.Equal(t, []string{"a.yml"}, bundle.Config.Include)
 }
+
+func TestProcessRootIncludesNotExists(t *testing.T) {
+	bundle := &bundle.Bundle{
+		Config: config.Root{
+			Path: t.TempDir(),
+			Include: []string{
+				"notexist.yml",
+			},
+		},
+	}
+	err := mutator.ProcessRootIncludes().Apply(context.Background(), bundle)
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "notexist.yml defined in 'include' section does not match any files")
+}
diff --git a/bundle/config/root.go b/bundle/config/root.go
index 28333e988..8e8325733 100644
--- a/bundle/config/root.go
+++ b/bundle/config/root.go
@@ -118,7 +118,7 @@ func (r *Root) Load(path string) error {
 	}
 	err = yaml.Unmarshal(raw, r)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to load %s: %w", path, err)
 	}
 
 	r.Path = filepath.Dir(path)
diff --git a/bundle/tests/include_invalid/bundle.yml b/bundle/tests/include_invalid/bundle.yml
new file mode 100644
index 000000000..f59e2ae0a
--- /dev/null
+++ b/bundle/tests/include_invalid/bundle.yml
@@ -0,0 +1,5 @@
+bundle:
+  name: include_invalid
+
+include:
+  - notexists.yml
diff --git a/bundle/tests/include_test.go b/bundle/tests/include_test.go
new file mode 100644
index 000000000..d704b8380
--- /dev/null
+++ b/bundle/tests/include_test.go
@@ -0,0 +1,34 @@
+package config_tests
+
+import (
+	"context"
+	"path/filepath"
+	"sort"
+	"testing"
+
+	"github.com/databricks/cli/bundle"
+	"github.com/databricks/cli/bundle/config/mutator"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"golang.org/x/exp/maps"
+)
+
+func TestIncludeInvalid(t *testing.T) {
+	b, err := bundle.Load("./include_invalid")
+	require.NoError(t, err)
+	err = bundle.Apply(context.Background(), b, bundle.Seq(mutator.DefaultMutators()...))
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "notexists.yml defined in 'include' section does not match any files")
+}
+
+func TestIncludeWithGlob(t *testing.T) {
+	b := load(t, "./include_with_glob")
+
+	keys := maps.Keys(b.Config.Resources.Jobs)
+	sort.Strings(keys)
+	assert.Equal(t, []string{"my_job"}, keys)
+
+	job := b.Config.Resources.Jobs["my_job"]
+	assert.Equal(t, "1", job.ID)
+	assert.Equal(t, "include_with_glob/job.yml", filepath.ToSlash(job.ConfigFilePath))
+}
diff --git a/bundle/tests/include_with_glob/bundle.yml b/bundle/tests/include_with_glob/bundle.yml
new file mode 100644
index 000000000..b1d078f9c
--- /dev/null
+++ b/bundle/tests/include_with_glob/bundle.yml
@@ -0,0 +1,7 @@
+bundle:
+  name: include_with_glob
+
+include:
+  - "*.yml"
+  - "?.yml"
+  - "[a-z].yml"
diff --git a/bundle/tests/include_with_glob/job.yml b/bundle/tests/include_with_glob/job.yml
new file mode 100644
index 000000000..3d609c529
--- /dev/null
+++ b/bundle/tests/include_with_glob/job.yml
@@ -0,0 +1,4 @@
+resources:
+  jobs:
+    my_job:
+      id: 1