diff --git a/client/pluginmanager/drivermanager/instance.go b/client/pluginmanager/drivermanager/instance.go
index 5196ff8dd..40f985c4c 100644
--- a/client/pluginmanager/drivermanager/instance.go
+++ b/client/pluginmanager/drivermanager/instance.go
@@ -186,18 +186,28 @@ func (i *instanceManager) dispense() (plugin drivers.DriverPlugin, err error) {
 	}
 
 	var pluginInstance loader.PluginInstance
+	dispenseFn := func() (loader.PluginInstance, error) {
+		return i.loader.Dispense(i.id.Name, i.id.PluginType, i.pluginConfig, i.logger)
+	}
 
 	if reattach, ok := i.fetchReattach(); ok {
 		// Reattach to existing plugin
 		pluginInstance, err = i.loader.Reattach(i.id.Name, i.id.PluginType, reattach)
+
+		// If reattachment fails, get a new plugin instance
+		if err != nil {
+			i.logger.Warn("failed to reattach to plugin, starting new instance", "err", err)
+			pluginInstance, err = dispenseFn()
+		}
 	} else {
 		// Get an instance of the plugin
-		pluginInstance, err = i.loader.Dispense(i.id.Name, i.id.PluginType, i.pluginConfig, i.logger)
+		pluginInstance, err = dispenseFn()
 	}
+
 	if err != nil {
 		// Retry as the error just indicates the singleton has exited
 		if err == singleton.SingletonPluginExited {
-			pluginInstance, err = i.loader.Dispense(i.id.Name, i.id.PluginType, i.pluginConfig, i.logger)
+			pluginInstance, err = dispenseFn()
 		}
 
 		// If we still have an error there is a real problem
diff --git a/client/pluginmanager/drivermanager/instance_test.go b/client/pluginmanager/drivermanager/instance_test.go
new file mode 100644
index 000000000..80af8b641
--- /dev/null
+++ b/client/pluginmanager/drivermanager/instance_test.go
@@ -0,0 +1,123 @@
+package drivermanager
+
+import (
+	"context"
+	"fmt"
+	"testing"
+
+	log "github.com/hashicorp/go-hclog"
+	"github.com/hashicorp/go-plugin"
+	"github.com/hashicorp/nomad/helper/pluginutils/loader"
+	"github.com/hashicorp/nomad/helper/pluginutils/singleton"
+	"github.com/hashicorp/nomad/helper/testlog"
+	"github.com/hashicorp/nomad/plugins/base"
+	dtu "github.com/hashicorp/nomad/plugins/drivers/testutils"
+	"github.com/stretchr/testify/mock"
+	"github.com/stretchr/testify/require"
+)
+
+type mockedCatalog struct {
+	mock.Mock
+}
+
+func (m *mockedCatalog) Dispense(name, pluginType string, cfg *base.AgentConfig, logger log.Logger) (loader.PluginInstance, error) {
+	args := m.Called(name, pluginType, cfg, logger)
+	return loader.MockBasicExternalPlugin(&dtu.MockDriver{}, "0.1.0"), args.Error(0)
+}
+
+func (m *mockedCatalog) Reattach(name, pluginType string, config *plugin.ReattachConfig) (loader.PluginInstance, error) {
+	args := m.Called(name, pluginType, config)
+	return loader.MockBasicExternalPlugin(&dtu.MockDriver{}, "0.1.0"), args.Error(0)
+}
+
+func (m *mockedCatalog) Catalog() map[string][]*base.PluginInfoResponse {
+	m.Called()
+	return map[string][]*base.PluginInfoResponse{
+		base.PluginTypeDriver: {&base.PluginInfoResponse{Name: "mock", Type: base.PluginTypeDriver}},
+	}
+}
+
+func (m *mockedCatalog) resetMock() {
+	m.ExpectedCalls = []*mock.Call{}
+	m.Calls = []mock.Call{}
+}
+
+func TestInstanceManager_dispense(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	cat := new(mockedCatalog)
+	cat.Test(t)
+	var fetchRet bool
+	i := &instanceManager{
+		logger:               testlog.HCLogger(t),
+		ctx:                  ctx,
+		cancel:               cancel,
+		loader:               cat,
+		storeReattach:        func(*plugin.ReattachConfig) error { return nil },
+		fetchReattach:        func() (*plugin.ReattachConfig, bool) { return nil, fetchRet },
+		pluginConfig:         &base.AgentConfig{},
+		id:                   &loader.PluginID{Name: "mock", PluginType: base.PluginTypeDriver},
+		updateNodeFromDriver: noopUpdater,
+		eventHandlerFactory:  noopEventHandlerFactory,
+		firstFingerprintCh:   make(chan struct{}),
+	}
+	require := require.New(t)
+
+	// First test the happy path, no reattach config is stored, plugin dispenses without error
+	fetchRet = false
+	cat.On("Dispense", mock.Anything, mock.Anything, mock.Anything, mock.Anything).Return(nil)
+	plug, err := i.dispense()
+	require.NoError(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 1)
+	cat.AssertNumberOfCalls(t, "Reattach", 0)
+
+	// Dispensing a second time should not dispense a new plugin from the catalog, but reuse the existing
+	plug2, err := i.dispense()
+	require.NoError(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 1)
+	cat.AssertNumberOfCalls(t, "Reattach", 0)
+	require.Same(plug, plug2)
+
+	// If the plugin has exited test that the manager attempts to retry dispense
+	cat.resetMock()
+	i.plugin = nil
+	cat.On("Dispense", mock.Anything, mock.Anything, mock.Anything, mock.Anything).Return(singleton.SingletonPluginExited)
+	_, err = i.dispense()
+	require.Error(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 2)
+	cat.AssertNumberOfCalls(t, "Reattach", 0)
+
+	// Test that when a reattach config exists it attempts plugin reattachment
+	// First case is when plugin reattachment is successful
+	fetchRet = true
+	cat.resetMock()
+	i.plugin = nil
+	cat.On("Dispense", mock.Anything, mock.Anything, mock.Anything, mock.Anything).Return(nil)
+	cat.On("Reattach", mock.Anything, mock.Anything, mock.Anything).Return(nil)
+	plug, err = i.dispense()
+	require.NoError(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 0)
+	cat.AssertNumberOfCalls(t, "Reattach", 1)
+	// Dispensing a second time should not dispense a new plugin from the catalog
+	plug2, err = i.dispense()
+	require.NoError(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 0)
+	cat.AssertNumberOfCalls(t, "Reattach", 1)
+	require.Same(plug, plug2)
+
+	// Finally test when reattachment fails. A new plugin should be dispensed
+	cat.resetMock()
+	i.plugin = nil
+	cat.On("Dispense", mock.Anything, mock.Anything, mock.Anything, mock.Anything).Return(nil)
+	cat.On("Reattach", mock.Anything, mock.Anything, mock.Anything).Return(fmt.Errorf("failed to dispense"))
+	plug, err = i.dispense()
+	require.NoError(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 1)
+	cat.AssertNumberOfCalls(t, "Reattach", 1)
+	// Dispensing a second time should not dispense a new plugin from the catalog
+	plug2, err = i.dispense()
+	require.NoError(err)
+	cat.AssertNumberOfCalls(t, "Dispense", 1)
+	cat.AssertNumberOfCalls(t, "Reattach", 1)
+	require.Same(plug, plug2)
+
+}