diff --git a/app/server.go b/app/server.go
index d32caa1672..dd403b37bf 100644
--- a/app/server.go
+++ b/app/server.go
@@ -188,6 +188,18 @@ func NewServer(options ...Option) (*Server, error) {
 		s.InitEmailBatching()
 	})
 
+	// Start plugin health check job
+	pluginsEnvironment := s.PluginsEnvironment
+	if pluginsEnvironment != nil {
+		pluginsEnvironment.InitPluginHealthCheckJob(*s.Config().PluginSettings.EnableHealthCheck)
+	}
+	s.AddConfigListener(func(_, c *model.Config) {
+		pluginsEnvironment := s.PluginsEnvironment
+		if pluginsEnvironment != nil {
+			pluginsEnvironment.InitPluginHealthCheckJob(*c.PluginSettings.EnableHealthCheck)
+		}
+	})
+
 	mlog.Info(fmt.Sprintf("Current version is %v (%v/%v/%v/%v)", model.CurrentVersion, model.BuildNumber, model.BuildDate, model.BuildHash, model.BuildHashEnterprise))
 	mlog.Info(fmt.Sprintf("Enterprise Enabled: %v", model.BuildEnterpriseReady))
 	pwd, _ := os.Getwd()
diff --git a/config/default.json b/config/default.json
index 8a8573aa3e..dce2188f2a 100644
--- a/config/default.json
+++ b/config/default.json
@@ -414,6 +414,7 @@
     "PluginSettings": {
         "Enable": true,
         "EnableUploads": false,
+        "EnableHealthCheck": true,
         "Directory": "./plugins",
         "ClientDirectory": "./client/plugins",
         "Plugins": {},
diff --git a/model/config.go b/model/config.go
index cc8025e2fb..4fe65b1197 100644
--- a/model/config.go
+++ b/model/config.go
@@ -2065,12 +2065,13 @@ type PluginState struct {
 }
 
 type PluginSettings struct {
-	Enable          *bool
-	EnableUploads   *bool   `restricted:"true"`
-	Directory       *string `restricted:"true"`
-	ClientDirectory *string `restricted:"true"`
-	Plugins         map[string]map[string]interface{}
-	PluginStates    map[string]*PluginState
+	Enable            *bool
+	EnableUploads     *bool   `restricted:"true"`
+	EnableHealthCheck *bool   `restricted:"true"`
+	Directory         *string `restricted:"true"`
+	ClientDirectory   *string `restricted:"true"`
+	Plugins           map[string]map[string]interface{}
+	PluginStates      map[string]*PluginState
 }
 
 func (s *PluginSettings) SetDefaults() {
@@ -2082,6 +2083,10 @@ func (s *PluginSettings) SetDefaults() {
 		s.EnableUploads = NewBool(false)
 	}
 
+	if s.EnableHealthCheck == nil {
+		s.EnableHealthCheck = NewBool(true)
+	}
+
 	if s.Directory == nil {
 		s.Directory = NewString(PLUGIN_SETTINGS_DEFAULT_DIRECTORY)
 	}
diff --git a/plugin/environment.go b/plugin/environment.go
index fdcbb227a3..0e8e6f1397 100644
--- a/plugin/environment.go
+++ b/plugin/environment.go
@@ -31,11 +31,13 @@ type activePlugin struct {
 // It is meant for use by the Mattermost server to manipulate, interact with and report on the set
 // of active plugins.
 type Environment struct {
-	activePlugins   sync.Map
-	logger          *mlog.Logger
-	newAPIImpl      apiImplCreatorFunc
-	pluginDir       string
-	webappPluginDir string
+	activePlugins        sync.Map
+	pluginHealthStatuses sync.Map
+	pluginHealthCheckJob *PluginHealthCheckJob
+	logger               *mlog.Logger
+	newAPIImpl           apiImplCreatorFunc
+	pluginDir            string
+	webappPluginDir      string
 }
 
 func NewEnvironment(newAPIImpl apiImplCreatorFunc, pluginDir string, webappPluginDir string, logger *mlog.Logger) (*Environment, error) {
@@ -227,6 +229,15 @@ func (env *Environment) Activate(id string) (manifest *model.Manifest, activated
 		ap.supervisor = sup
 
 		componentActivated = true
+
+		var h *PluginHealthStatus
+		if health, ok := env.pluginHealthStatuses.Load(id); ok {
+			h = health.(*PluginHealthStatus)
+		} else {
+			h = newPluginHealthStatus()
+			env.pluginHealthStatuses.Store(id, h)
+		}
+		h.Crashed = false
 	}
 
 	if !componentActivated {
@@ -256,6 +267,30 @@ func (env *Environment) Deactivate(id string) bool {
 	return true
 }
 
+// RestartPlugin deactivates, then activates the plugin with the given id.
+func (env *Environment) RestartPlugin(id string) error {
+	env.Deactivate(id)
+	_, _, err := env.Activate(id)
+	return err
+}
+
+// UpdatePluginHealthStatus accepts a callback to edit the stored health status of the plugin.
+func (env *Environment) UpdatePluginHealthStatus(id string, callback func(*PluginHealthStatus)) {
+	if h, ok := env.pluginHealthStatuses.Load(id); ok {
+		callback(h.(*PluginHealthStatus))
+	}
+}
+
+// CheckPluginHealthStatus checks if the plugin is in a failed state, based on information gathered from previous health checks.
+func (env *Environment) CheckPluginHealthStatus(id string) error {
+	if h, ok := env.pluginHealthStatuses.Load(id); ok {
+		if h.(*PluginHealthStatus).Crashed {
+			return h.(*PluginHealthStatus).lastError
+		}
+	}
+	return nil
+}
+
 // Shutdown deactivates all plugins and gracefully shuts down the environment.
 func (env *Environment) Shutdown() {
 	env.activePlugins.Range(func(key, value interface{}) bool {
diff --git a/plugin/health_check.go b/plugin/health_check.go
new file mode 100644
index 0000000000..94e721a078
--- /dev/null
+++ b/plugin/health_check.go
@@ -0,0 +1,156 @@
+// Copyright (c) 2017-present Mattermost, Inc. All Rights Reserved.
+// See License.txt for license information.
+
+package plugin
+
+import (
+	"fmt"
+	"time"
+
+	"github.com/mattermost/mattermost-server/mlog"
+)
+
+const (
+	HEALTH_CHECK_INTERVAL         = 30 // seconds. How often the health check should run
+	HEALTH_CHECK_DISABLE_DURATION = 60 // minutes. How long we wait for num fails to incur before disabling the plugin
+	HEALTH_CHECK_PING_FAIL_LIMIT  = 3  // How many times we call RPC ping in a row before it is considered a failure
+	HEALTH_CHECK_RESTART_LIMIT    = 3  // How many times we restart a plugin before we disable it
+)
+
+type PluginHealthCheckJob struct {
+	cancel    chan struct{}
+	cancelled chan struct{}
+	env       *Environment
+}
+
+type PluginHealthStatus struct {
+	Crashed        bool
+	failTimeStamps []time.Time
+	lastError      error
+}
+
+// InitPluginHealthCheckJob starts a new job if one is not running and is set to enabled, or kills an existing one if set to disabled.
+func (env *Environment) InitPluginHealthCheckJob(enable bool) {
+	// Config is set to enable. No job exists, start a new job.
+	if enable && env.pluginHealthCheckJob == nil {
+		job := newPluginHealthCheckJob(env)
+		env.pluginHealthCheckJob = job
+		job.Start()
+	}
+
+	// Config is set to disable. Job exists, kill existing job.
+	if !enable && env.pluginHealthCheckJob != nil {
+		env.pluginHealthCheckJob.Cancel()
+		env.pluginHealthCheckJob = nil
+	}
+}
+
+// Start continuously runs health checks on all active plugins, on a timer.
+func (job *PluginHealthCheckJob) Start() {
+	interval := time.Duration(HEALTH_CHECK_INTERVAL) * time.Second
+	mlog.Debug(fmt.Sprintf("Plugin health check job starting. Sending health check pings every %v seconds.", interval))
+
+	go func() {
+		defer close(job.cancelled)
+
+		ticker := time.NewTicker(interval)
+		defer func() {
+			ticker.Stop()
+		}()
+
+		for {
+			select {
+			case <-ticker.C:
+				activePlugins := job.env.Active()
+				for _, plugin := range activePlugins {
+					job.checkPlugin(plugin.Manifest.Id)
+				}
+			case <-job.cancel:
+				return
+			}
+		}
+	}()
+}
+
+// checkPlugin determines the plugin's health status, then handles the error or success case.
+func (job *PluginHealthCheckJob) checkPlugin(id string) {
+	p, ok := job.env.activePlugins.Load(id)
+	if !ok {
+		return
+	}
+	ap := p.(activePlugin)
+
+	if _, ok := job.env.pluginHealthStatuses.Load(id); !ok {
+		job.env.pluginHealthStatuses.Store(id, newPluginHealthStatus())
+	}
+
+	sup := ap.supervisor
+	if sup == nil {
+		return
+	}
+
+	pluginErr := sup.PerformHealthCheck()
+
+	if pluginErr != nil {
+		mlog.Error(fmt.Sprintf("Health check failed for plugin %s, error: %s", id, pluginErr.Error()))
+		job.handleHealthCheckFail(id, pluginErr)
+	}
+}
+
+// handleHealthCheckFail restarts or deactivates the plugin based on how many times it has failed in a configured amount of time.
+func (job *PluginHealthCheckJob) handleHealthCheckFail(id string, err error) {
+	health, ok := job.env.pluginHealthStatuses.Load(id)
+	if !ok {
+		return
+	}
+	h := health.(*PluginHealthStatus)
+
+	// Append current failure before checking for deactivate vs restart action
+	h.failTimeStamps = append(h.failTimeStamps, time.Now())
+	h.lastError = err
+
+	if shouldDeactivatePlugin(h) {
+		h.failTimeStamps = []time.Time{}
+		h.Crashed = true
+		mlog.Debug(fmt.Sprintf("Deactivating plugin due to multiple crashes `%s`", id))
+		job.env.Deactivate(id)
+	} else {
+		mlog.Debug(fmt.Sprintf("Restarting plugin due to failed health check `%s`", id))
+		if err := job.env.RestartPlugin(id); err != nil {
+			mlog.Error(fmt.Sprintf("Failed to restart plugin `%s`: %s", id, err.Error()))
+		}
+	}
+}
+
+func newPluginHealthCheckJob(env *Environment) *PluginHealthCheckJob {
+	return &PluginHealthCheckJob{
+		cancel:    make(chan struct{}),
+		cancelled: make(chan struct{}),
+		env:       env,
+	}
+}
+
+func (job *PluginHealthCheckJob) Cancel() {
+	close(job.cancel)
+	<-job.cancelled
+}
+
+func newPluginHealthStatus() *PluginHealthStatus {
+	return &PluginHealthStatus{failTimeStamps: []time.Time{}, Crashed: false}
+}
+
+// shouldDeactivatePlugin determines if a plugin needs to be deactivated after certain criteria is met.
+//
+// The criteria is based on if the plugin has consistently failed during the configured number of restarts, within the configured time window.
+func shouldDeactivatePlugin(h *PluginHealthStatus) bool {
+	if len(h.failTimeStamps) >= HEALTH_CHECK_RESTART_LIMIT {
+		index := len(h.failTimeStamps) - HEALTH_CHECK_RESTART_LIMIT
+		t := h.failTimeStamps[index]
+		now := time.Now()
+		elapsed := now.Sub(t).Minutes()
+		if elapsed <= HEALTH_CHECK_DISABLE_DURATION {
+			return true
+		}
+	}
+	return false
+}
diff --git a/plugin/health_check_test.go b/plugin/health_check_test.go
new file mode 100644
index 0000000000..9c45337a0d
--- /dev/null
+++ b/plugin/health_check_test.go
@@ -0,0 +1,207 @@
+// Copyright (c) 2017-present Mattermost, Inc. All Rights Reserved.
+// See License.txt for license information.
+
+package plugin
+
+import (
+	"io/ioutil"
+	"os"
+	"path/filepath"
+	"testing"
+	"time"
+
+	"github.com/mattermost/mattermost-server/mlog"
+	"github.com/mattermost/mattermost-server/model"
+	"github.com/mattermost/mattermost-server/utils"
+	"github.com/stretchr/testify/require"
+)
+
+func TestPluginHealthCheck(t *testing.T) {
+	for name, f := range map[string]func(*testing.T){
+		"PluginHealthCheck_Success":                 testPluginHealthCheck_Success,
+		"PluginHealthCheck_PluginPanicProcessCheck": testPluginHealthCheck_PluginPanicProcessCheck,
+		"PluginHealthCheck_RPCPingFail":             testPluginHealthCheck_RPCPingFail,
+	} {
+		t.Run(name, f)
+	}
+}
+
+func testPluginHealthCheck_Success(t *testing.T) {
+	dir, err := ioutil.TempDir("", "")
+	require.NoError(t, err)
+	defer os.RemoveAll(dir)
+
+	backend := filepath.Join(dir, "backend.exe")
+	utils.CompileGo(t, `
+		package main
+
+		import (
+			"github.com/mattermost/mattermost-server/plugin"
+		)
+
+		type MyPlugin struct {
+			plugin.MattermostPlugin
+		}
+
+		func main() {
+			plugin.ClientMain(&MyPlugin{})
+		}
+	`, backend)
+
+	err = ioutil.WriteFile(filepath.Join(dir, "plugin.json"), []byte(`{"id": "foo", "backend": {"executable": "backend.exe"}}`), 0600)
+	require.NoError(t, err)
+
+	bundle := model.BundleInfoForPath(dir)
+	log := mlog.NewLogger(&mlog.LoggerConfiguration{
+		EnableConsole: true,
+		ConsoleJson:   true,
+		ConsoleLevel:  "error",
+		EnableFile:    false,
+	})
+
+	supervisor, err := newSupervisor(bundle, log, nil)
+	require.Nil(t, err)
+	require.NotNil(t, supervisor)
+
+	err = supervisor.PerformHealthCheck()
+	require.Nil(t, err)
+}
+
+func testPluginHealthCheck_PluginPanicProcessCheck(t *testing.T) {
+	dir, err := ioutil.TempDir("", "")
+	require.NoError(t, err)
+	defer os.RemoveAll(dir)
+
+	backend := filepath.Join(dir, "backend.exe")
+	utils.CompileGo(t, `
+		package main
+
+		import (
+			"github.com/mattermost/mattermost-server/model"
+			"github.com/mattermost/mattermost-server/plugin"
+		)
+
+		type MyPlugin struct {
+			plugin.MattermostPlugin
+		}
+
+		func (p *MyPlugin) MessageWillBePosted(c *plugin.Context, post *model.Post) (*model.Post, string) {
+			panic("Uncaught error")
+		}
+
+		func main() {
+			plugin.ClientMain(&MyPlugin{})
+		}
+	`, backend)
+
+	err = ioutil.WriteFile(filepath.Join(dir, "plugin.json"), []byte(`{"id": "foo", "backend": {"executable": "backend.exe"}}`), 0600)
+	require.NoError(t, err)
+
+	bundle := model.BundleInfoForPath(dir)
+	log := mlog.NewLogger(&mlog.LoggerConfiguration{
+		EnableConsole: true,
+		ConsoleJson:   true,
+		ConsoleLevel:  "error",
+		EnableFile:    false,
+	})
+
+	supervisor, err := newSupervisor(bundle, log, nil)
+	require.Nil(t, err)
+	require.NotNil(t, supervisor)
+
+	err = supervisor.PerformHealthCheck()
+	require.Nil(t, err)
+
+	supervisor.hooks.MessageWillBePosted(&Context{}, &model.Post{})
+	time.Sleep(10 * time.Millisecond)
+
+	err = supervisor.PerformHealthCheck()
+	require.NotNil(t, err)
+	require.Equal(t, "Plugin process not found, or not responding", err.Error())
+}
+
+func testPluginHealthCheck_RPCPingFail(t *testing.T) {
+	dir, err := ioutil.TempDir("", "")
+	require.NoError(t, err)
+	defer os.RemoveAll(dir)
+
+	backend := filepath.Join(dir, "backend.exe")
+	utils.CompileGo(t, `
+		package main
+
+		import (
+			"github.com/mattermost/mattermost-server/plugin"
+		)
+
+		type MyPlugin struct {
+			plugin.MattermostPlugin
+		}
+
+		func main() {
+			plugin.ClientMain(&MyPlugin{})
+		}
+	`, backend)
+
+	err = ioutil.WriteFile(filepath.Join(dir, "plugin.json"), []byte(`{"id": "foo", "backend": {"executable": "backend.exe"}}`), 0600)
+	require.NoError(t, err)
+
+	bundle := model.BundleInfoForPath(dir)
+	log := mlog.NewLogger(&mlog.LoggerConfiguration{
+		EnableConsole: true,
+		ConsoleJson:   true,
+		ConsoleLevel:  "error",
+		EnableFile:    false,
+	})
+
+	supervisor, err := newSupervisor(bundle, log, nil)
+	require.Nil(t, err)
+	require.NotNil(t, supervisor)
+
+	err = supervisor.PerformHealthCheck()
+	require.Nil(t, err)
+
+	c, err := supervisor.client.Client()
+	require.Nil(t, err)
+	c.Close()
+
+	err = supervisor.PerformHealthCheck()
+	require.NotNil(t, err)
+	require.Equal(t, "Plugin RPC connection is not responding", err.Error())
+}
+
+func TestShouldDeactivatePlugin(t *testing.T) {
+	h := newPluginHealthStatus()
+	require.NotNil(t, h)
+
+	// No failures, don't restart
+	result := shouldDeactivatePlugin(h)
+	require.Equal(t, false, result)
+
+	now := time.Now()
+
+	// Failures are recent enough to restart
+	h = newPluginHealthStatus()
+	h.failTimeStamps = append(h.failTimeStamps, now.Add(-HEALTH_CHECK_DISABLE_DURATION*0.2*time.Minute))
+	h.failTimeStamps = append(h.failTimeStamps, now.Add(-HEALTH_CHECK_DISABLE_DURATION*0.1*time.Minute))
+	h.failTimeStamps = append(h.failTimeStamps, now)
+
+	result = shouldDeactivatePlugin(h)
+	require.Equal(t, true, result)
+
+	// Failures are too spaced out to warrant a restart
+	h = newPluginHealthStatus()
+	h.failTimeStamps = append(h.failTimeStamps, now.Add(-HEALTH_CHECK_DISABLE_DURATION*2*time.Minute))
+	h.failTimeStamps = append(h.failTimeStamps, now.Add(-HEALTH_CHECK_DISABLE_DURATION*1*time.Minute))
+	h.failTimeStamps = append(h.failTimeStamps, now)
+
+	result = shouldDeactivatePlugin(h)
+	require.Equal(t, false, result)
+
+	// Not enough failures are present to warrant a restart
+	h = newPluginHealthStatus()
+	h.failTimeStamps = append(h.failTimeStamps, now.Add(-HEALTH_CHECK_DISABLE_DURATION*0.1*time.Minute))
+	h.failTimeStamps = append(h.failTimeStamps, now)
+
+	result = shouldDeactivatePlugin(h)
+	require.Equal(t, false, result)
+}
diff --git a/plugin/supervisor.go b/plugin/supervisor.go
index 70e6636e3c..25faa978f7 100644
--- a/plugin/supervisor.go
+++ b/plugin/supervisor.go
@@ -4,11 +4,14 @@
 package plugin
 
 import (
+	"errors"
 	"fmt"
+	"os"
 	"os/exec"
 	"path/filepath"
 	"runtime"
 	"strings"
+	"syscall"
 	"time"
 
 	plugin "github.com/hashicorp/go-plugin"
@@ -20,6 +23,7 @@ type supervisor struct {
 	client      *plugin.Client
 	hooks       Hooks
 	implemented [TotalHooksId]bool
+	pid         int
 }
 
 func newSupervisor(pluginInfo *model.BundleInfo, parentLogger *mlog.Logger, apiImpl API) (retSupervisor *supervisor, retErr error) {
@@ -53,10 +57,12 @@ func newSupervisor(pluginInfo *model.BundleInfo, parentLogger *mlog.Logger, apiI
 	}
 	executable = filepath.Join(pluginInfo.Path, executable)
 
+	cmd := exec.Command(executable)
+
 	sup.client = plugin.NewClient(&plugin.ClientConfig{
 		HandshakeConfig: handshake,
 		Plugins:         pluginMap,
-		Cmd:             exec.Command(executable),
+		Cmd:             cmd,
 		SyncStdout:      wrappedLogger.With(mlog.String("source", "plugin_stdout")).StdLogWriter(),
 		SyncStderr:      wrappedLogger.With(mlog.String("source", "plugin_stderr")).StdLogWriter(),
 		Logger:          hclogAdaptedLogger,
@@ -68,6 +74,8 @@ func newSupervisor(pluginInfo *model.BundleInfo, parentLogger *mlog.Logger, apiI
 		return nil, err
 	}
 
+	sup.pid = cmd.Process.Pid
+
 	raw, err := rpcClient.Dispense("hooks")
 	if err != nil {
 		return nil, err
@@ -103,6 +111,55 @@ func (sup *supervisor) Hooks() Hooks {
 	return sup.hooks
 }
 
+// PerformHealthCheck checks the plugin through a process check, an RPC ping, and a HealthCheck hook call.
+func (sup *supervisor) PerformHealthCheck() error {
+	if procErr := sup.CheckProcess(); procErr != nil {
+		mlog.Debug(fmt.Sprintf("Error checking plugin process, error: %s", procErr.Error()))
+		return errors.New("Plugin process not found, or not responding")
+	}
+
+	if pingErr := sup.Ping(); pingErr != nil {
+		for pingFails := 1; pingFails < HEALTH_CHECK_PING_FAIL_LIMIT; pingFails++ {
+			pingErr = sup.Ping()
+			if pingErr == nil {
+				break
+			}
+		}
+		if pingErr != nil {
+			mlog.Debug(fmt.Sprintf("Error pinging plugin, error: %s", pingErr.Error()))
+			return fmt.Errorf("Plugin RPC connection is not responding")
+		}
+	}
+
+	return nil
+}
+
+// Ping checks that the RPC connection with the plugin is alive and healthy.
+func (sup *supervisor) Ping() error {
+	client, err := sup.client.Client()
+
+	if err != nil {
+		return err
+	}
+
+	return client.Ping()
+}
+
+// CheckProcess checks if the plugin process's PID exists and can respond to a signal.
+func (sup *supervisor) CheckProcess() error {
+	process, err := os.FindProcess(sup.pid)
+	if err != nil {
+		return err
+	}
+
+	err = process.Signal(syscall.Signal(0))
+	if err != nil {
+		return err
+	}
+
+	return nil
+}
+
 func (sup *supervisor) Implements(hookId int) bool {
 	return sup.implemented[hookId]
 }