diff --git a/bundle/bundle.go b/bundle/bundle.go
index 0147883c..06c68fe8 100644
--- a/bundle/bundle.go
+++ b/bundle/bundle.go
@@ -7,6 +7,7 @@
 package bundle
 
 import (
+	"context"
 	"fmt"
 	"os"
 	"path/filepath"
@@ -16,6 +17,7 @@ import (
 	"github.com/databricks/cli/folders"
 	"github.com/databricks/cli/libs/git"
 	"github.com/databricks/cli/libs/locker"
+	"github.com/databricks/cli/libs/log"
 	"github.com/databricks/cli/libs/terraform"
 	"github.com/databricks/databricks-sdk-go"
 	sdkconfig "github.com/databricks/databricks-sdk-go/config"
@@ -45,7 +47,7 @@ type Bundle struct {
 
 const ExtraIncludePathsKey string = "DATABRICKS_BUNDLE_INCLUDES"
 
-func Load(path string) (*Bundle, error) {
+func Load(ctx context.Context, path string) (*Bundle, error) {
 	bundle := &Bundle{}
 	stat, err := os.Stat(path)
 	if err != nil {
@@ -56,6 +58,7 @@ func Load(path string) (*Bundle, error) {
 		_, hasIncludePathEnv := os.LookupEnv(ExtraIncludePathsKey)
 		_, hasBundleRootEnv := os.LookupEnv(envBundleRoot)
 		if hasIncludePathEnv && hasBundleRootEnv && stat.IsDir() {
+			log.Debugf(ctx, "No bundle configuration; using bundle root: %s", path)
 			bundle.Config = config.Root{
 				Path: path,
 				Bundle: config.Bundle{
@@ -66,6 +69,7 @@ func Load(path string) (*Bundle, error) {
 		}
 		return nil, err
 	}
+	log.Debugf(ctx, "Loading bundle configuration from: %s", configFile)
 	err = bundle.Config.Load(configFile)
 	if err != nil {
 		return nil, err
@@ -75,19 +79,19 @@ func Load(path string) (*Bundle, error) {
 
 // MustLoad returns a bundle configuration.
 // It returns an error if a bundle was not found or could not be loaded.
-func MustLoad() (*Bundle, error) {
+func MustLoad(ctx context.Context) (*Bundle, error) {
 	root, err := mustGetRoot()
 	if err != nil {
 		return nil, err
 	}
 
-	return Load(root)
+	return Load(ctx, root)
 }
 
 // TryLoad returns a bundle configuration if there is one, but doesn't fail if there isn't one.
 // It returns an error if a bundle was found but could not be loaded.
 // It returns a `nil` bundle if a bundle was not found.
-func TryLoad() (*Bundle, error) {
+func TryLoad(ctx context.Context) (*Bundle, error) {
 	root, err := tryGetRoot()
 	if err != nil {
 		return nil, err
@@ -98,7 +102,7 @@ func TryLoad() (*Bundle, error) {
 		return nil, nil
 	}
 
-	return Load(root)
+	return Load(ctx, root)
 }
 
 func (b *Bundle) WorkspaceClient() *databricks.WorkspaceClient {
diff --git a/bundle/bundle_test.go b/bundle/bundle_test.go
index 18550f4f..ac947500 100644
--- a/bundle/bundle_test.go
+++ b/bundle/bundle_test.go
@@ -1,6 +1,7 @@
 package bundle
 
 import (
+	"context"
 	"os"
 	"path/filepath"
 	"testing"
@@ -10,13 +11,13 @@ import (
 )
 
 func TestLoadNotExists(t *testing.T) {
-	b, err := Load("/doesntexist")
+	b, err := Load(context.Background(), "/doesntexist")
 	assert.True(t, os.IsNotExist(err))
 	assert.Nil(t, b)
 }
 
 func TestLoadExists(t *testing.T) {
-	b, err := Load("./tests/basic")
+	b, err := Load(context.Background(), "./tests/basic")
 	require.Nil(t, err)
 	assert.Equal(t, "basic", b.Config.Bundle.Name)
 }
@@ -27,7 +28,7 @@ func TestBundleCacheDir(t *testing.T) {
 	require.NoError(t, err)
 	f1.Close()
 
-	bundle, err := Load(projectDir)
+	bundle, err := Load(context.Background(), projectDir)
 	require.NoError(t, err)
 
 	// Artificially set environment.
@@ -51,7 +52,7 @@ func TestBundleCacheDirOverride(t *testing.T) {
 	require.NoError(t, err)
 	f1.Close()
 
-	bundle, err := Load(projectDir)
+	bundle, err := Load(context.Background(), projectDir)
 	require.NoError(t, err)
 
 	// Artificially set environment.
@@ -70,39 +71,39 @@ func TestBundleCacheDirOverride(t *testing.T) {
 
 func TestBundleMustLoadSuccess(t *testing.T) {
 	t.Setenv(envBundleRoot, "./tests/basic")
-	b, err := MustLoad()
+	b, err := MustLoad(context.Background())
 	require.NoError(t, err)
 	assert.Equal(t, "tests/basic", filepath.ToSlash(b.Config.Path))
 }
 
 func TestBundleMustLoadFailureWithEnv(t *testing.T) {
 	t.Setenv(envBundleRoot, "./tests/doesntexist")
-	_, err := MustLoad()
+	_, err := MustLoad(context.Background())
 	require.Error(t, err, "not a directory")
 }
 
 func TestBundleMustLoadFailureIfNotFound(t *testing.T) {
 	chdir(t, t.TempDir())
-	_, err := MustLoad()
+	_, err := MustLoad(context.Background())
 	require.Error(t, err, "unable to find bundle root")
 }
 
 func TestBundleTryLoadSuccess(t *testing.T) {
 	t.Setenv(envBundleRoot, "./tests/basic")
-	b, err := TryLoad()
+	b, err := TryLoad(context.Background())
 	require.NoError(t, err)
 	assert.Equal(t, "tests/basic", filepath.ToSlash(b.Config.Path))
 }
 
 func TestBundleTryLoadFailureWithEnv(t *testing.T) {
 	t.Setenv(envBundleRoot, "./tests/doesntexist")
-	_, err := TryLoad()
+	_, err := TryLoad(context.Background())
 	require.Error(t, err, "not a directory")
 }
 
 func TestBundleTryLoadOkIfNotFound(t *testing.T) {
 	chdir(t, t.TempDir())
-	b, err := TryLoad()
+	b, err := TryLoad(context.Background())
 	assert.NoError(t, err)
 	assert.Nil(t, b)
 }
diff --git a/bundle/root_test.go b/bundle/root_test.go
index e85c4fdc..0c4c46aa 100644
--- a/bundle/root_test.go
+++ b/bundle/root_test.go
@@ -1,6 +1,7 @@
 package bundle
 
 import (
+	"context"
 	"os"
 	"path/filepath"
 	"testing"
@@ -108,7 +109,7 @@ func TestLoadYamlWhenIncludesEnvPresent(t *testing.T) {
 	chdir(t, filepath.Join(".", "tests", "basic"))
 	t.Setenv(ExtraIncludePathsKey, "test")
 
-	bundle, err := MustLoad()
+	bundle, err := MustLoad(context.Background())
 	assert.NoError(t, err)
 	assert.Equal(t, "basic", bundle.Config.Bundle.Name)
 
@@ -123,7 +124,7 @@ func TestLoadDefautlBundleWhenNoYamlAndRootAndIncludesEnvPresent(t *testing.T) {
 	t.Setenv(envBundleRoot, dir)
 	t.Setenv(ExtraIncludePathsKey, "test")
 
-	bundle, err := MustLoad()
+	bundle, err := MustLoad(context.Background())
 	assert.NoError(t, err)
 	assert.Equal(t, dir, bundle.Config.Path)
 }
@@ -133,7 +134,7 @@ func TestErrorIfNoYamlNoRootEnvAndIncludesEnvPresent(t *testing.T) {
 	chdir(t, dir)
 	t.Setenv(ExtraIncludePathsKey, "test")
 
-	_, err := MustLoad()
+	_, err := MustLoad(context.Background())
 	assert.Error(t, err)
 }
 
@@ -142,6 +143,6 @@ func TestErrorIfNoYamlNoIncludesEnvAndRootEnvPresent(t *testing.T) {
 	chdir(t, dir)
 	t.Setenv(envBundleRoot, dir)
 
-	_, err := MustLoad()
+	_, err := MustLoad(context.Background())
 	assert.Error(t, err)
 }
diff --git a/bundle/tests/bundle/wheel_test.go b/bundle/tests/bundle/wheel_test.go
index bfc1fa04..ee745773 100644
--- a/bundle/tests/bundle/wheel_test.go
+++ b/bundle/tests/bundle/wheel_test.go
@@ -12,11 +12,12 @@ import (
 )
 
 func TestBundlePythonWheelBuild(t *testing.T) {
-	b, err := bundle.Load("./python_wheel")
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, "./python_wheel")
 	require.NoError(t, err)
 
 	m := phases.Build()
-	err = m.Apply(context.Background(), b)
+	err = m.Apply(ctx, b)
 	require.NoError(t, err)
 
 	matches, err := filepath.Glob("python_wheel/my_test_code/dist/my_test_code-*.whl")
@@ -24,16 +25,17 @@ func TestBundlePythonWheelBuild(t *testing.T) {
 	require.Equal(t, 1, len(matches))
 
 	match := libraries.MatchWithArtifacts()
-	err = match.Apply(context.Background(), b)
+	err = match.Apply(ctx, b)
 	require.NoError(t, err)
 }
 
 func TestBundlePythonWheelBuildAutoDetect(t *testing.T) {
-	b, err := bundle.Load("./python_wheel_no_artifact")
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, "./python_wheel_no_artifact")
 	require.NoError(t, err)
 
 	m := phases.Build()
-	err = m.Apply(context.Background(), b)
+	err = m.Apply(ctx, b)
 	require.NoError(t, err)
 
 	matches, err := filepath.Glob("python_wheel/my_test_code/dist/my_test_code-*.whl")
@@ -41,19 +43,20 @@ func TestBundlePythonWheelBuildAutoDetect(t *testing.T) {
 	require.Equal(t, 1, len(matches))
 
 	match := libraries.MatchWithArtifacts()
-	err = match.Apply(context.Background(), b)
+	err = match.Apply(ctx, b)
 	require.NoError(t, err)
 }
 
 func TestBundlePythonWheelWithDBFSLib(t *testing.T) {
-	b, err := bundle.Load("./python_wheel_dbfs_lib")
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, "./python_wheel_dbfs_lib")
 	require.NoError(t, err)
 
 	m := phases.Build()
-	err = m.Apply(context.Background(), b)
+	err = m.Apply(ctx, b)
 	require.NoError(t, err)
 
 	match := libraries.MatchWithArtifacts()
-	err = match.Apply(context.Background(), b)
+	err = match.Apply(ctx, b)
 	require.NoError(t, err)
 }
diff --git a/bundle/tests/conflicting_resource_ids_test.go b/bundle/tests/conflicting_resource_ids_test.go
index b75e3753..704683ad 100644
--- a/bundle/tests/conflicting_resource_ids_test.go
+++ b/bundle/tests/conflicting_resource_ids_test.go
@@ -13,24 +13,27 @@ import (
 )
 
 func TestConflictingResourceIdsNoSubconfig(t *testing.T) {
-	_, err := bundle.Load("./conflicting_resource_ids/no_subconfigurations")
+	ctx := context.Background()
+	_, err := bundle.Load(ctx, "./conflicting_resource_ids/no_subconfigurations")
 	bundleConfigPath := filepath.FromSlash("conflicting_resource_ids/no_subconfigurations/databricks.yml")
 	assert.ErrorContains(t, err, fmt.Sprintf("multiple resources named foo (job at %s, pipeline at %s)", bundleConfigPath, bundleConfigPath))
 }
 
 func TestConflictingResourceIdsOneSubconfig(t *testing.T) {
-	b, err := bundle.Load("./conflicting_resource_ids/one_subconfiguration")
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, "./conflicting_resource_ids/one_subconfiguration")
 	require.NoError(t, err)
-	err = bundle.Apply(context.Background(), b, bundle.Seq(mutator.DefaultMutators()...))
+	err = bundle.Apply(ctx, b, bundle.Seq(mutator.DefaultMutators()...))
 	bundleConfigPath := filepath.FromSlash("conflicting_resource_ids/one_subconfiguration/databricks.yml")
 	resourcesConfigPath := filepath.FromSlash("conflicting_resource_ids/one_subconfiguration/resources.yml")
 	assert.ErrorContains(t, err, fmt.Sprintf("multiple resources named foo (job at %s, pipeline at %s)", bundleConfigPath, resourcesConfigPath))
 }
 
 func TestConflictingResourceIdsTwoSubconfigs(t *testing.T) {
-	b, err := bundle.Load("./conflicting_resource_ids/two_subconfigurations")
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, "./conflicting_resource_ids/two_subconfigurations")
 	require.NoError(t, err)
-	err = bundle.Apply(context.Background(), b, bundle.Seq(mutator.DefaultMutators()...))
+	err = bundle.Apply(ctx, b, bundle.Seq(mutator.DefaultMutators()...))
 	resources1ConfigPath := filepath.FromSlash("conflicting_resource_ids/two_subconfigurations/resources1.yml")
 	resources2ConfigPath := filepath.FromSlash("conflicting_resource_ids/two_subconfigurations/resources2.yml")
 	assert.ErrorContains(t, err, fmt.Sprintf("multiple resources named foo (job at %s, pipeline at %s)", resources1ConfigPath, resources2ConfigPath))
diff --git a/bundle/tests/include_test.go b/bundle/tests/include_test.go
index 00aecb9f..eb09d1aa 100644
--- a/bundle/tests/include_test.go
+++ b/bundle/tests/include_test.go
@@ -14,9 +14,10 @@ import (
 )
 
 func TestIncludeInvalid(t *testing.T) {
-	b, err := bundle.Load("./include_invalid")
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, "./include_invalid")
 	require.NoError(t, err)
-	err = bundle.Apply(context.Background(), b, bundle.Seq(mutator.DefaultMutators()...))
+	err = bundle.Apply(ctx, 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")
 }
diff --git a/bundle/tests/loader.go b/bundle/tests/loader.go
index 42f1fc5b..056a82d9 100644
--- a/bundle/tests/loader.go
+++ b/bundle/tests/loader.go
@@ -10,9 +10,10 @@ import (
 )
 
 func load(t *testing.T, path string) *bundle.Bundle {
-	b, err := bundle.Load(path)
+	ctx := context.Background()
+	b, err := bundle.Load(ctx, path)
 	require.NoError(t, err)
-	err = bundle.Apply(context.Background(), b, bundle.Seq(mutator.DefaultMutators()...))
+	err = bundle.Apply(ctx, b, bundle.Seq(mutator.DefaultMutators()...))
 	require.NoError(t, err)
 	return b
 }
diff --git a/cmd/root/bundle.go b/cmd/root/bundle.go
index 8a3b5977..f691bbfc 100644
--- a/cmd/root/bundle.go
+++ b/cmd/root/bundle.go
@@ -1,6 +1,7 @@
 package root
 
 import (
+	"context"
 	"os"
 
 	"github.com/databricks/cli/bundle"
@@ -41,8 +42,9 @@ func getProfile(cmd *cobra.Command) (value string) {
 }
 
 // loadBundle loads the bundle configuration and applies default mutators.
-func loadBundle(cmd *cobra.Command, args []string, load func() (*bundle.Bundle, error)) (*bundle.Bundle, error) {
-	b, err := load()
+func loadBundle(cmd *cobra.Command, args []string, load func(ctx context.Context) (*bundle.Bundle, error)) (*bundle.Bundle, error) {
+	ctx := cmd.Context()
+	b, err := load(ctx)
 	if err != nil {
 		return nil, err
 	}
@@ -57,7 +59,6 @@ func loadBundle(cmd *cobra.Command, args []string, load func() (*bundle.Bundle,
 		b.Config.Workspace.Profile = profile
 	}
 
-	ctx := cmd.Context()
 	err = bundle.Apply(ctx, b, bundle.Seq(mutator.DefaultMutators()...))
 	if err != nil {
 		return nil, err
@@ -67,7 +68,7 @@ func loadBundle(cmd *cobra.Command, args []string, load func() (*bundle.Bundle,
 }
 
 // configureBundle loads the bundle configuration and configures it on the command's context.
-func configureBundle(cmd *cobra.Command, args []string, load func() (*bundle.Bundle, error)) error {
+func configureBundle(cmd *cobra.Command, args []string, load func(ctx context.Context) (*bundle.Bundle, error)) error {
 	b, err := loadBundle(cmd, args, load)
 	if err != nil {
 		return err
diff --git a/cmd/root/bundle_test.go b/cmd/root/bundle_test.go
index 4b44e019..4382cf22 100644
--- a/cmd/root/bundle_test.go
+++ b/cmd/root/bundle_test.go
@@ -39,7 +39,7 @@ func emptyCommand(t *testing.T) *cobra.Command {
 func setup(t *testing.T, cmd *cobra.Command, host string) *bundle.Bundle {
 	setupDatabricksCfg(t)
 
-	err := configureBundle(cmd, []string{"validate"}, func() (*bundle.Bundle, error) {
+	err := configureBundle(cmd, []string{"validate"}, func(_ context.Context) (*bundle.Bundle, error) {
 		return &bundle.Bundle{
 			Config: config.Root{
 				Bundle: config.Bundle{