diff --git a/internal/core/machine_test.go b/internal/core/machine_test.go
index 9a136a9a5..7fcef998a 100644
--- a/internal/core/machine_test.go
+++ b/internal/core/machine_test.go
@@ -60,6 +60,11 @@ func TestMachineSetEmptyId(t *testing.T) {
 	require.Nil(t, dbTarget)
 	require.Error(t, err)
 
+	// Verify the DataDir still exists (see below test for more detail on why)
+	dir, err := tm.DataDir()
+	require.NoError(t, err)
+	require.DirExists(t, dir.DataDir().String())
+
 	// Also check new id
 	dbTarget, err = tm.Client().GetTarget(tm.ctx,
 		&vagrant_server.GetTargetRequest{
@@ -74,6 +79,22 @@ func TestMachineSetEmptyId(t *testing.T) {
 	require.Error(t, err)
 }
 
+func TestMachineSetIdBlankThenSomethingPreservesDataDir(t *testing.T) {
+	tm, _ := TestMinimalMachine(t)
+
+	// Set empty id, followed by a temp id. This is the same thing that happens
+	// in the Docker provider's InitState action
+	require.NoError(t, tm.SetID(""))
+	require.NoError(t, tm.SetID("preparing"))
+
+	// The DataDir should still exist; the Docker provider relies on this
+	// behavior in order for its provisioning sentinel file handling to work
+	// properly.
+	dir, err := tm.DataDir()
+	require.NoError(t, err)
+	require.DirExists(t, dir.DataDir().String())
+}
+
 func TestMachineGetNonExistentBox(t *testing.T) {
 	tp := TestMinimalProject(t)
 	tm, _ := TestMachine(t, tp,
diff --git a/internal/core/project.go b/internal/core/project.go
index c27474ac6..6cc55ff83 100644
--- a/internal/core/project.go
+++ b/internal/core/project.go
@@ -231,8 +231,8 @@ func (p *Project) JobInfo() *component.JobInfo {
 	return p.jobInfo
 }
 
-// Load a project within the current basis. If the project is not found, it
-// will be created.
+// LoadTarget loads a target within the current project. If the target is not
+// found, it will be created.
 func (p *Project) LoadTarget(topts ...TargetOption) (t *Target, err error) {
 	p.m.Lock()
 	defer p.m.Unlock()
diff --git a/internal/core/target.go b/internal/core/target.go
index d41fd0dea..e0db5d089 100644
--- a/internal/core/target.go
+++ b/internal/core/target.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"fmt"
 	"os"
+	"path/filepath"
 	"strings"
 	"sync"
 	"time"
@@ -265,7 +266,19 @@ func (t *Target) Destroy() (err error) {
 	_, err = t.Client().DeleteTarget(t.ctx, &vagrant_server.DeleteTargetRequest{
 		Target: t.Ref().(*vagrant_plugin_sdk.Ref_Target),
 	})
-	os.RemoveAll(t.dir.DataDir().String())
+
+	// Remove all the files inside the datadir without wiping the datadir itself
+	files, err := filepath.Glob(filepath.Join(t.dir.DataDir().String(), "*"))
+	if err != nil {
+		return err
+	}
+	for _, file := range files {
+		rerr := os.RemoveAll(file)
+		if rerr != nil {
+			err = multierror.Append(err, rerr)
+		}
+	}
+
 	return
 }
 
diff --git a/internal/core/testing_basis.go b/internal/core/testing_basis.go
index f1052733b..a65f657e0 100644
--- a/internal/core/testing_basis.go
+++ b/internal/core/testing_basis.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"io/ioutil"
 	"os"
+	"path/filepath"
 
 	"github.com/hashicorp/vagrant-plugin-sdk/core"
 	coremocks "github.com/hashicorp/vagrant-plugin-sdk/core/mocks"
@@ -79,8 +80,20 @@ func TestBasis(t testing.T, opts ...BasisOption) (b *Basis) {
 	require.NoError(t, err)
 	t.Cleanup(func() { os.RemoveAll(td) })
 
-	projDir, err := datadir.NewBasis(td)
-	require.NoError(t, err)
+	mkSubdir := func(root, sub string) string {
+		sd := filepath.Join(root, sub)
+		require.NoError(t, os.Mkdir(sd, 0755))
+		return sd
+	}
+
+	projDir := &datadir.Basis{
+		Dir: datadir.NewBasicDir(
+			mkSubdir(td, "config"),
+			mkSubdir(td, "cache"),
+			mkSubdir(td, "data"),
+			mkSubdir(td, "temp"),
+		),
+	}
 
 	defaultOpts := []BasisOption{
 		WithClient(singleprocess.TestServer(t)),