diff --git a/bundle/config/mutator/configure_wsfs.go b/bundle/config/mutator/configure_wsfs.go
index 1d1bec5824..110e1a3819 100644
--- a/bundle/config/mutator/configure_wsfs.go
+++ b/bundle/config/mutator/configure_wsfs.go
@@ -5,14 +5,12 @@ import (
 	"strings"
 
 	"github.com/databricks/cli/bundle"
+	"github.com/databricks/cli/libs/dbr"
 	"github.com/databricks/cli/libs/diag"
-	"github.com/databricks/cli/libs/env"
 	"github.com/databricks/cli/libs/filer"
 	"github.com/databricks/cli/libs/vfs"
 )
 
-const envDatabricksRuntimeVersion = "DATABRICKS_RUNTIME_VERSION"
-
 type configureWSFS struct{}
 
 func ConfigureWSFS() bundle.Mutator {
@@ -32,7 +30,7 @@ func (m *configureWSFS) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagno
 	}
 
 	// The executable must be running on DBR.
-	if _, ok := env.Lookup(ctx, envDatabricksRuntimeVersion); !ok {
+	if !dbr.RunsOnRuntime(ctx) {
 		return nil
 	}
 
diff --git a/bundle/config/mutator/configure_wsfs_test.go b/bundle/config/mutator/configure_wsfs_test.go
new file mode 100644
index 0000000000..6f76293e08
--- /dev/null
+++ b/bundle/config/mutator/configure_wsfs_test.go
@@ -0,0 +1,65 @@
+package mutator_test
+
+import (
+	"context"
+	"runtime"
+	"testing"
+
+	"github.com/databricks/cli/bundle"
+	"github.com/databricks/cli/bundle/config/mutator"
+	"github.com/databricks/cli/libs/dbr"
+	"github.com/databricks/cli/libs/vfs"
+	"github.com/databricks/databricks-sdk-go/config"
+	"github.com/databricks/databricks-sdk-go/experimental/mocks"
+	"github.com/stretchr/testify/assert"
+)
+
+func mockBundleForConfigureWSFS(t *testing.T, syncRootPath string) *bundle.Bundle {
+	// The native path of the sync root on Windows will never match the /Workspace prefix,
+	// so the test case for nominal behavior will always fail.
+	if runtime.GOOS == "windows" {
+		t.Skip("this test is not applicable on Windows")
+	}
+
+	b := &bundle.Bundle{
+		SyncRoot: vfs.MustNew(syncRootPath),
+	}
+
+	w := mocks.NewMockWorkspaceClient(t)
+	w.WorkspaceClient.Config = &config.Config{}
+	b.SetWorkpaceClient(w.WorkspaceClient)
+
+	return b
+}
+
+func TestConfigureWSFS_SkipsIfNotWorkspacePrefix(t *testing.T) {
+	b := mockBundleForConfigureWSFS(t, "/foo")
+	originalSyncRoot := b.SyncRoot
+
+	ctx := context.Background()
+	diags := bundle.Apply(ctx, b, mutator.ConfigureWSFS())
+	assert.Empty(t, diags)
+	assert.Equal(t, originalSyncRoot, b.SyncRoot)
+}
+
+func TestConfigureWSFS_SkipsIfNotRunningOnRuntime(t *testing.T) {
+	b := mockBundleForConfigureWSFS(t, "/Workspace/foo")
+	originalSyncRoot := b.SyncRoot
+
+	ctx := context.Background()
+	ctx = dbr.MockRuntime(ctx, false)
+	diags := bundle.Apply(ctx, b, mutator.ConfigureWSFS())
+	assert.Empty(t, diags)
+	assert.Equal(t, originalSyncRoot, b.SyncRoot)
+}
+
+func TestConfigureWSFS_SwapSyncRoot(t *testing.T) {
+	b := mockBundleForConfigureWSFS(t, "/Workspace/foo")
+	originalSyncRoot := b.SyncRoot
+
+	ctx := context.Background()
+	ctx = dbr.MockRuntime(ctx, true)
+	diags := bundle.Apply(ctx, b, mutator.ConfigureWSFS())
+	assert.Empty(t, diags)
+	assert.NotEqual(t, originalSyncRoot, b.SyncRoot)
+}
diff --git a/cmd/root/root.go b/cmd/root/root.go
index 7059586f30..e6f66f126f 100644
--- a/cmd/root/root.go
+++ b/cmd/root/root.go
@@ -11,6 +11,7 @@ import (
 
 	"github.com/databricks/cli/internal/build"
 	"github.com/databricks/cli/libs/cmdio"
+	"github.com/databricks/cli/libs/dbr"
 	"github.com/databricks/cli/libs/log"
 	"github.com/spf13/cobra"
 )
@@ -73,6 +74,9 @@ func New(ctx context.Context) *cobra.Command {
 		// get the context back
 		ctx = cmd.Context()
 
+		// Detect if the CLI is running on DBR and store this on the context.
+		ctx = dbr.DetectRuntime(ctx)
+
 		// Configure our user agent with the command that's about to be executed.
 		ctx = withCommandInUserAgent(ctx, cmd)
 		ctx = withCommandExecIdInUserAgent(ctx)
diff --git a/libs/dbr/context.go b/libs/dbr/context.go
new file mode 100644
index 0000000000..7512c0fe27
--- /dev/null
+++ b/libs/dbr/context.go
@@ -0,0 +1,49 @@
+package dbr
+
+import "context"
+
+// key is a package-local type to use for context keys.
+//
+// Using an unexported type for context keys prevents key collisions across
+// packages since external packages cannot create values of this type.
+type key int
+
+const (
+	// dbrKey is the context key for the detection result.
+	// The value of 1 is arbitrary and can be any number.
+	// Other keys in the same package must have different values.
+	dbrKey = key(1)
+)
+
+// DetectRuntime detects whether or not the current
+// process is running inside a Databricks Runtime environment.
+// It return a new context with the detection result set.
+func DetectRuntime(ctx context.Context) context.Context {
+	if v := ctx.Value(dbrKey); v != nil {
+		panic("dbr.DetectRuntime called twice on the same context")
+	}
+	return context.WithValue(ctx, dbrKey, detect(ctx))
+}
+
+// MockRuntime is a helper function to mock the detection result.
+// It returns a new context with the detection result set.
+func MockRuntime(ctx context.Context, b bool) context.Context {
+	if v := ctx.Value(dbrKey); v != nil {
+		panic("dbr.MockRuntime called twice on the same context")
+	}
+	return context.WithValue(ctx, dbrKey, b)
+}
+
+// RunsOnRuntime returns the detection result from the context.
+// It expects a context returned by [DetectRuntime] or [MockRuntime].
+//
+// We store this value in a context to avoid having to use either
+// a global variable, passing a boolean around everywhere, or
+// performing the same detection multiple times.
+func RunsOnRuntime(ctx context.Context) bool {
+	v := ctx.Value(dbrKey)
+	if v == nil {
+		panic("dbr.RunsOnRuntime called without calling dbr.DetectRuntime first")
+	}
+	return v.(bool)
+}
diff --git a/libs/dbr/context_test.go b/libs/dbr/context_test.go
new file mode 100644
index 0000000000..fc53cf130e
--- /dev/null
+++ b/libs/dbr/context_test.go
@@ -0,0 +1,59 @@
+package dbr
+
+import (
+	"context"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestContext_DetectRuntimePanics(t *testing.T) {
+	ctx := context.Background()
+
+	// Run detection.
+	ctx = DetectRuntime(ctx)
+
+	// Expect a panic if the detection is run twice.
+	assert.Panics(t, func() {
+		ctx = DetectRuntime(ctx)
+	})
+}
+
+func TestContext_MockRuntimePanics(t *testing.T) {
+	ctx := context.Background()
+
+	// Run detection.
+	ctx = MockRuntime(ctx, true)
+
+	// Expect a panic if the mock function is run twice.
+	assert.Panics(t, func() {
+		MockRuntime(ctx, true)
+	})
+}
+
+func TestContext_RunsOnRuntimePanics(t *testing.T) {
+	ctx := context.Background()
+
+	// Expect a panic if the detection is not run.
+	assert.Panics(t, func() {
+		RunsOnRuntime(ctx)
+	})
+}
+
+func TestContext_RunsOnRuntime(t *testing.T) {
+	ctx := context.Background()
+
+	// Run detection.
+	ctx = DetectRuntime(ctx)
+
+	// Expect no panic because detection has run.
+	assert.NotPanics(t, func() {
+		RunsOnRuntime(ctx)
+	})
+}
+
+func TestContext_RunsOnRuntimeWithMock(t *testing.T) {
+	ctx := context.Background()
+	assert.True(t, RunsOnRuntime(MockRuntime(ctx, true)))
+	assert.False(t, RunsOnRuntime(MockRuntime(ctx, false)))
+}
diff --git a/libs/dbr/detect.go b/libs/dbr/detect.go
new file mode 100644
index 0000000000..d8b4dfe20e
--- /dev/null
+++ b/libs/dbr/detect.go
@@ -0,0 +1,35 @@
+package dbr
+
+import (
+	"context"
+	"os"
+	"runtime"
+
+	"github.com/databricks/cli/libs/env"
+)
+
+// Dereference [os.Stat] to allow mocking in tests.
+var statFunc = os.Stat
+
+// detect returns true if the current process is running on a Databricks Runtime.
+// Its return value is meant to be cached in the context.
+func detect(ctx context.Context) bool {
+	// Databricks Runtime implies Linux.
+	// Return early on other operating systems.
+	if runtime.GOOS != "linux" {
+		return false
+	}
+
+	// Databricks Runtime always has the DATABRICKS_RUNTIME_VERSION environment variable set.
+	if value, ok := env.Lookup(ctx, "DATABRICKS_RUNTIME_VERSION"); !ok || value == "" {
+		return false
+	}
+
+	// Expect to see a "/databricks" directory.
+	if fi, err := statFunc("/databricks"); err != nil || !fi.IsDir() {
+		return false
+	}
+
+	// All checks passed.
+	return true
+}
diff --git a/libs/dbr/detect_test.go b/libs/dbr/detect_test.go
new file mode 100644
index 0000000000..3a4a43a73b
--- /dev/null
+++ b/libs/dbr/detect_test.go
@@ -0,0 +1,83 @@
+package dbr
+
+import (
+	"context"
+	"io/fs"
+	"runtime"
+	"testing"
+
+	"github.com/databricks/cli/libs/env"
+	"github.com/databricks/cli/libs/fakefs"
+	"github.com/stretchr/testify/assert"
+)
+
+func requireLinux(t *testing.T) {
+	if runtime.GOOS != "linux" {
+		t.Skipf("skipping test on %s", runtime.GOOS)
+	}
+}
+
+func configureStatFunc(t *testing.T, fi fs.FileInfo, err error) {
+	originalFunc := statFunc
+	statFunc = func(name string) (fs.FileInfo, error) {
+		assert.Equal(t, "/databricks", name)
+		return fi, err
+	}
+
+	t.Cleanup(func() {
+		statFunc = originalFunc
+	})
+}
+
+func TestDetect_NotLinux(t *testing.T) {
+	if runtime.GOOS == "linux" {
+		t.Skip("skipping test on Linux OS")
+	}
+
+	ctx := context.Background()
+	assert.False(t, detect(ctx))
+}
+
+func TestDetect_Env(t *testing.T) {
+	requireLinux(t)
+
+	// Configure other checks to pass.
+	configureStatFunc(t, fakefs.FileInfo{FakeDir: true}, nil)
+
+	t.Run("empty", func(t *testing.T) {
+		ctx := env.Set(context.Background(), "DATABRICKS_RUNTIME_VERSION", "")
+		assert.False(t, detect(ctx))
+	})
+
+	t.Run("non-empty cluster", func(t *testing.T) {
+		ctx := env.Set(context.Background(), "DATABRICKS_RUNTIME_VERSION", "15.4")
+		assert.True(t, detect(ctx))
+	})
+
+	t.Run("non-empty serverless", func(t *testing.T) {
+		ctx := env.Set(context.Background(), "DATABRICKS_RUNTIME_VERSION", "client.1.13")
+		assert.True(t, detect(ctx))
+	})
+}
+
+func TestDetect_Stat(t *testing.T) {
+	requireLinux(t)
+
+	// Configure other checks to pass.
+	ctx := env.Set(context.Background(), "DATABRICKS_RUNTIME_VERSION", "non-empty")
+
+	t.Run("error", func(t *testing.T) {
+		configureStatFunc(t, nil, fs.ErrNotExist)
+		assert.False(t, detect(ctx))
+	})
+
+	t.Run("not a directory", func(t *testing.T) {
+		configureStatFunc(t, fakefs.FileInfo{}, nil)
+		assert.False(t, detect(ctx))
+	})
+
+	t.Run("directory", func(t *testing.T) {
+		configureStatFunc(t, fakefs.FileInfo{FakeDir: true}, nil)
+		assert.True(t, detect(ctx))
+	})
+}
diff --git a/libs/fakefs/fakefs.go b/libs/fakefs/fakefs.go
new file mode 100644
index 0000000000..2f4756970d
--- /dev/null
+++ b/libs/fakefs/fakefs.go
@@ -0,0 +1,55 @@
+package fakefs
+
+import (
+	"io/fs"
+	"time"
+)
+
+// DirEntry is a fake implementation of [fs.DirEntry].
+type DirEntry struct {
+	FileInfo
+}
+
+func (entry DirEntry) Type() fs.FileMode {
+	typ := fs.ModePerm
+	if entry.FakeDir {
+		typ |= fs.ModeDir
+	}
+	return typ
+}
+
+func (entry DirEntry) Info() (fs.FileInfo, error) {
+	return entry.FileInfo, nil
+}
+
+// FileInfo is a fake implementation of [fs.FileInfo].
+type FileInfo struct {
+	FakeName string
+	FakeSize int64
+	FakeDir  bool
+	FakeMode fs.FileMode
+}
+
+func (info FileInfo) Name() string {
+	return info.FakeName
+}
+
+func (info FileInfo) Size() int64 {
+	return info.FakeSize
+}
+
+func (info FileInfo) Mode() fs.FileMode {
+	return info.FakeMode
+}
+
+func (info FileInfo) ModTime() time.Time {
+	return time.Now()
+}
+
+func (info FileInfo) IsDir() bool {
+	return info.FakeDir
+}
+
+func (info FileInfo) Sys() any {
+	return nil
+}