diff --git a/agent/agent.go b/agent/agent.go
index 40a50dcb1..6bac3eb9a 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -1104,7 +1104,7 @@ func (a *Agent) setupNodeID(config *config.RuntimeConfig) error {
 	}
 
 	// For dev mode we have no filesystem access so just make one.
-	if a.config.DevMode {
+	if a.config.DataDir == "" {
 		id, err := a.makeNodeID()
 		if err != nil {
 			return err
@@ -1320,8 +1320,17 @@ func (a *Agent) ShutdownAgent() error {
 
 	// Stop the proxy manager
 	if a.proxyManager != nil {
-		if err := a.proxyManager.Close(); err != nil {
-			a.logger.Printf("[WARN] agent: error shutting down proxy manager: %s", err)
+		// If persistence is disabled (implies DevMode but a subset of DevMode) then
+		// don't leave the proxies running since the agent will not be able to
+		// recover them later.
+		if a.config.DataDir == "" {
+			if err := a.proxyManager.Kill(); err != nil {
+				a.logger.Printf("[WARN] agent: error shutting down proxy manager: %s", err)
+			}
+		} else {
+			if err := a.proxyManager.Close(); err != nil {
+				a.logger.Printf("[WARN] agent: error shutting down proxy manager: %s", err)
+			}
 		}
 	}
 
@@ -1720,7 +1729,7 @@ func (a *Agent) AddService(service *structs.NodeService, chkTypes []*structs.Che
 	a.State.AddService(service, token)
 
 	// Persist the service to a file
-	if persist && !a.config.DevMode {
+	if persist && a.config.DataDir != "" {
 		if err := a.persistService(service); err != nil {
 			return err
 		}
@@ -2019,7 +2028,7 @@ func (a *Agent) AddCheck(check *structs.HealthCheck, chkType *structs.CheckType,
 	}
 
 	// Persist the check
-	if persist && !a.config.DevMode {
+	if persist && a.config.DataDir != "" {
 		return a.persistCheck(check, chkType)
 	}
 
@@ -2118,7 +2127,7 @@ func (a *Agent) AddProxy(proxy *structs.ConnectManagedProxy, persist bool,
 	}
 
 	// Persist the proxy
-	if persist && !a.config.DevMode {
+	if persist && a.config.DataDir != "" {
 		return a.persistProxy(proxyState)
 	}
 	return nil
@@ -2177,7 +2186,7 @@ func (a *Agent) RemoveProxy(proxyID string, persist bool) error {
 		return err
 	}
 
-	if persist && !a.config.DevMode {
+	if persist && a.config.DataDir != "" {
 		return a.purgeProxy(proxyID)
 	}
 
@@ -2298,7 +2307,7 @@ func (a *Agent) updateTTLCheck(checkID types.CheckID, status, output string) err
 	check.SetStatus(status, output)
 
 	// We don't write any files in dev mode so bail here.
-	if a.config.DevMode {
+	if a.config.DataDir == "" {
 		return nil
 	}
 
diff --git a/agent/proxy/daemon.go b/agent/proxy/daemon.go
index aa7bc3f53..ca11ecce0 100644
--- a/agent/proxy/daemon.go
+++ b/agent/proxy/daemon.go
@@ -34,9 +34,9 @@ type Daemon struct {
 	// be a Cmd that isn't yet started.
 	Command *exec.Cmd
 
-	// ProxyId is the ID of the proxy service. This is required for API
+	// ProxyID is the ID of the proxy service. This is required for API
 	// requests (along with the token) and is passed via env var.
-	ProxyId string
+	ProxyID string
 
 	// ProxyToken is the special local-only ACL token that allows a proxy
 	// to communicate to the Connect-specific endpoints.
@@ -121,6 +121,11 @@ func (p *Daemon) keepAlive(stopCh <-chan struct{}, exitedCh chan<- struct{}) {
 			if !attemptsDeadline.IsZero() && time.Now().After(attemptsDeadline) {
 				attempts = 0
 			}
+			// Set ourselves a deadline - we have to make it at least this long before
+			// we come around the loop to consider it to have been a "successful"
+			// daemon startup and rest the counter above. Note that if the daemon
+			// fails before this, we reset the deadline to zero below so that backoff
+			// sleeps in the loop don't count as "success" time.
 			attemptsDeadline = time.Now().Add(DaemonRestartHealthy)
 			attempts++
 
@@ -136,6 +141,10 @@ func (p *Daemon) keepAlive(stopCh <-chan struct{}, exitedCh chan<- struct{}) {
 				}
 
 				if waitTime > 0 {
+					// If we are waiting, reset the success deadline so we don't
+					// accidentally interpret backoff sleep as successful runtime.
+					attemptsDeadline = time.Time{}
+
 					p.Logger.Printf(
 						"[WARN] agent/proxy: waiting %s before restarting daemon",
 						waitTime)
@@ -224,15 +233,21 @@ func (p *Daemon) keepAlive(stopCh <-chan struct{}, exitedCh chan<- struct{}) {
 func (p *Daemon) start() (*os.Process, error) {
 	cmd := *p.Command
 
-	// Add the proxy token to the environment. We first copy the env because
-	// it is a slice and therefore the "copy" above will only copy the slice
-	// reference. We allocate an exactly sized slice.
-	cmd.Env = make([]string, len(p.Command.Env), len(p.Command.Env)+1)
+	// Add the proxy token to the environment. We first copy the env because it is
+	// a slice and therefore the "copy" above will only copy the slice reference.
+	// We allocate an exactly sized slice.
+	//
+	// Note that anything we add to the Env here is NOT persisted in the snapshot
+	// which only looks at p.Command.Env so it needs to be reconstructible exactly
+	// from data in the snapshot otherwise.
+	cmd.Env = make([]string, len(p.Command.Env), len(p.Command.Env)+2)
 	copy(cmd.Env, p.Command.Env)
 	cmd.Env = append(cmd.Env,
-		fmt.Sprintf("%s=%s", EnvProxyId, p.ProxyId),
+		fmt.Sprintf("%s=%s", EnvProxyID, p.ProxyID),
 		fmt.Sprintf("%s=%s", EnvProxyToken, p.ProxyToken))
 
+	// Update the Daemon env
+
 	// Args must always contain a 0 entry which is usually the executed binary.
 	// To be safe and a bit more robust we default this, but only to prevent
 	// a panic below.
@@ -366,6 +381,7 @@ func (p *Daemon) Equal(raw Proxy) bool {
 
 	// We compare equality on a subset of the command configuration
 	return p.ProxyToken == p2.ProxyToken &&
+		p.ProxyID == p2.ProxyID &&
 		p.Command.Path == p2.Command.Path &&
 		p.Command.Dir == p2.Command.Dir &&
 		reflect.DeepEqual(p.Command.Args, p2.Command.Args) &&
@@ -389,6 +405,7 @@ func (p *Daemon) MarshalSnapshot() map[string]interface{} {
 		"CommandDir":  p.Command.Dir,
 		"CommandEnv":  p.Command.Env,
 		"ProxyToken":  p.ProxyToken,
+		"ProxyID":     p.ProxyID,
 	}
 }
 
@@ -404,6 +421,7 @@ func (p *Daemon) UnmarshalSnapshot(m map[string]interface{}) error {
 
 	// Set the basic fields
 	p.ProxyToken = s.ProxyToken
+	p.ProxyID = s.ProxyID
 	p.Command = &exec.Cmd{
 		Path: s.CommandPath,
 		Args: s.CommandArgs,
@@ -435,7 +453,7 @@ func (p *Daemon) UnmarshalSnapshot(m map[string]interface{}) error {
 // within the manager snapshot and is restored automatically.
 type daemonSnapshot struct {
 	// Pid of the process. This is the only value actually required to
-	// regain mangement control. The remainder values are for Equal.
+	// regain management control. The remainder values are for Equal.
 	Pid int
 
 	// Command information
@@ -448,4 +466,6 @@ type daemonSnapshot struct {
 	// store the hash of the token but for now we need the full token in
 	// case the process dies and has to be restarted.
 	ProxyToken string
+
+	ProxyID string
 }
diff --git a/agent/proxy/daemon_test.go b/agent/proxy/daemon_test.go
index 089592278..b2b9f5dfd 100644
--- a/agent/proxy/daemon_test.go
+++ b/agent/proxy/daemon_test.go
@@ -32,7 +32,7 @@ func TestDaemonStartStop(t *testing.T) {
 
 	d := &Daemon{
 		Command:    helperProcess("start-stop", path),
-		ProxyId:    "tubes",
+		ProxyID:    "tubes",
 		ProxyToken: uuid,
 		Logger:     testLogger,
 	}
@@ -495,6 +495,19 @@ func TestDaemonEqual(t *testing.T) {
 			true,
 		},
 
+		{
+			"Different proxy ID",
+			&Daemon{
+				Command: &exec.Cmd{Path: "/foo"},
+				ProxyID: "web",
+			},
+			&Daemon{
+				Command: &exec.Cmd{Path: "/foo"},
+				ProxyID: "db",
+			},
+			false,
+		},
+
 		{
 			"Different path",
 			&Daemon{
@@ -568,6 +581,7 @@ func TestDaemonMarshalSnapshot(t *testing.T) {
 			"basic",
 			&Daemon{
 				Command: &exec.Cmd{Path: "/foo"},
+				ProxyID: "web",
 				process: &os.Process{Pid: 42},
 			},
 			map[string]interface{}{
@@ -577,6 +591,7 @@ func TestDaemonMarshalSnapshot(t *testing.T) {
 				"CommandDir":  "",
 				"CommandEnv":  []string(nil),
 				"ProxyToken":  "",
+				"ProxyID":     "web",
 			},
 		},
 	}
diff --git a/agent/proxy/manager.go b/agent/proxy/manager.go
index a8a941753..410a6b5d1 100644
--- a/agent/proxy/manager.go
+++ b/agent/proxy/manager.go
@@ -423,7 +423,7 @@ func (m *Manager) newProxy(mp *local.ManagedProxy) (Proxy, error) {
 
 		// Build the daemon structure
 		proxy.Command = &cmd
-		proxy.ProxyId = id
+		proxy.ProxyID = id
 		proxy.ProxyToken = mp.ProxyToken
 		return proxy, nil
 
diff --git a/agent/proxy/proxy.go b/agent/proxy/proxy.go
index c8a1dd18a..91f44dc99 100644
--- a/agent/proxy/proxy.go
+++ b/agent/proxy/proxy.go
@@ -12,10 +12,10 @@ import (
 )
 
 const (
-	// EnvProxyId is the name of the environment variable that is set for
+	// EnvProxyID is the name of the environment variable that is set for
 	// managed proxies containing the proxy service ID. This is required along
 	// with the token to make API requests related to the proxy.
-	EnvProxyId = "CONNECT_PROXY_ID"
+	EnvProxyID = "CONNECT_PROXY_ID"
 
 	// EnvProxyToken is the name of the environment variable that is passed
 	// to managed proxies containing the proxy token.
diff --git a/agent/proxy/proxy_test.go b/agent/proxy/proxy_test.go
index a04bb65d5..0a9237319 100644
--- a/agent/proxy/proxy_test.go
+++ b/agent/proxy/proxy_test.go
@@ -81,7 +81,7 @@ func TestHelperProcess(t *testing.T) {
 
 		path := args[0]
 		var data []byte
-		data = append(data, []byte(os.Getenv(EnvProxyId))...)
+		data = append(data, []byte(os.Getenv(EnvProxyID))...)
 		data = append(data, ':')
 		data = append(data, []byte(os.Getenv(EnvProxyToken))...)
 
diff --git a/command/connect/proxy/proxy.go b/command/connect/proxy/proxy.go
index 91df04025..48ea721d5 100644
--- a/command/connect/proxy/proxy.go
+++ b/command/connect/proxy/proxy.go
@@ -125,7 +125,7 @@ func (c *cmd) Run(args []string) int {
 
 	// Load the proxy ID and token from env vars if they're set
 	if c.proxyID == "" {
-		c.proxyID = os.Getenv(proxyAgent.EnvProxyId)
+		c.proxyID = os.Getenv(proxyAgent.EnvProxyID)
 	}
 	if c.http.Token() == "" {
 		c.http.SetToken(os.Getenv(proxyAgent.EnvProxyToken))