diff --git a/agent/agent.go b/agent/agent.go
index dc72fa0407..d28be94385 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -333,11 +333,11 @@ func (a *Agent) run(ctx context.Context) {
 					a.config.SessionTracker.SessionError(err)
 				}
 
-				log.G(ctx).WithError(err).Error("agent: session failed")
 				backoff = initialSessionFailureBackoff + 2*backoff
 				if backoff > maxSessionFailureBackoff {
 					backoff = maxSessionFailureBackoff
 				}
+				log.G(ctx).WithError(err).WithField("backoff", backoff).Errorf("agent: session failed")
 			}
 
 			if err := session.close(); err != nil {
diff --git a/agent/session.go b/agent/session.go
index 0c00c4f1bf..b1038c263e 100644
--- a/agent/session.go
+++ b/agent/session.go
@@ -65,6 +65,8 @@ func newSession(ctx context.Context, agent *Agent, delay time.Duration, sessionI
 		grpc.WithTransportCredentials(agent.config.Credentials),
 		grpc.WithTimeout(dispatcherRPCTimeout),
 	)
+	log.G(ctx).Infof("manager selected by agent for new session: %v", cc.Peer())
+
 	if err != nil {
 		s.errs <- err
 		return s
@@ -77,6 +79,7 @@ func newSession(ctx context.Context, agent *Agent, delay time.Duration, sessionI
 
 func (s *session) run(ctx context.Context, delay time.Duration, description *api.NodeDescription) {
 	timer := time.NewTimer(delay) // delay before registering.
+	log.G(ctx).Infof("waiting %v before registering session", delay)
 	defer timer.Stop()
 	select {
 	case <-timer.C:
@@ -166,15 +169,23 @@ func (s *session) heartbeat(ctx context.Context) error {
 	heartbeat := time.NewTimer(1) // send out a heartbeat right away
 	defer heartbeat.Stop()
 
+	fields := logrus.Fields{
+		"sessionID": s.sessionID,
+		"method":    "(*session).heartbeat",
+	}
+
 	for {
 		select {
 		case <-heartbeat.C:
 			heartbeatCtx, cancel := context.WithTimeout(ctx, dispatcherRPCTimeout)
+			// TODO(anshul) log manager info in all logs in this function.
+			log.G(ctx).WithFields(fields).Debugf("sending heartbeat to manager %v with timeout %v", s.conn.Peer(), dispatcherRPCTimeout)
 			resp, err := client.Heartbeat(heartbeatCtx, &api.HeartbeatRequest{
 				SessionID: s.sessionID,
 			})
 			cancel()
 			if err != nil {
+				log.G(ctx).WithFields(fields).WithError(err).Errorf("heartbeat to manager %v failed", s.conn.Peer())
 				if grpc.Code(err) == codes.NotFound {
 					err = errNodeNotRegistered
 				}
@@ -182,6 +193,8 @@ func (s *session) heartbeat(ctx context.Context) error {
 				return err
 			}
 
+			log.G(ctx).WithFields(fields).Debugf("heartbeat successful to manager %v, next heartbeat period: %v", s.conn.Peer(), resp.Period)
+
 			heartbeat.Reset(resp.Period)
 		case <-s.closed:
 			return errSessionClosed
@@ -408,7 +421,7 @@ func (s *session) sendError(err error) {
 	}
 }
 
-// close closing session. It should be called only in <-session.errs branch
+// close the given session. It should be called only in <-session.errs branch
 // of event loop, or when cleaning up the agent.
 func (s *session) close() error {
 	s.closeOnce.Do(func() {
diff --git a/connectionbroker/broker.go b/connectionbroker/broker.go
index 43b384ab2a..a5510a9ff0 100644
--- a/connectionbroker/broker.go
+++ b/connectionbroker/broker.go
@@ -58,6 +58,7 @@ func (b *Broker) Select(dialOpts ...grpc.DialOption) (*Conn, error) {
 // connection.
 func (b *Broker) SelectRemote(dialOpts ...grpc.DialOption) (*Conn, error) {
 	peer, err := b.remotes.Select()
+
 	if err != nil {
 		return nil, err
 	}
@@ -98,6 +99,11 @@ type Conn struct {
 	peer    api.Peer
 }
 
+// Peer returns the peer for this Conn.
+func (c *Conn) Peer() api.Peer {
+	return c.peer
+}
+
 // Close closes the client connection if it is a remote connection. It also
 // records a positive experience with the remote peer if success is true,
 // otherwise it records a negative experience. If a local connection is in use,
diff --git a/manager/dispatcher/dispatcher.go b/manager/dispatcher/dispatcher.go
index 13d68293ae..12c2a81e34 100644
--- a/manager/dispatcher/dispatcher.go
+++ b/manager/dispatcher/dispatcher.go
@@ -195,6 +195,9 @@ func getWeightedPeers(cluster Cluster) []*api.WeightedPeer {
 // Run runs dispatcher tasks which should be run on leader dispatcher.
 // Dispatcher can be stopped with cancelling ctx or calling Stop().
 func (d *Dispatcher) Run(ctx context.Context) error {
+	ctx = log.WithModule(ctx, "dispatcher")
+	log.G(ctx).Info("dispatcher starting")
+
 	d.taskUpdatesLock.Lock()
 	d.taskUpdates = make(map[string]*api.TaskStatus)
 	d.taskUpdatesLock.Unlock()
@@ -208,7 +211,6 @@ func (d *Dispatcher) Run(ctx context.Context) error {
 		d.mu.Unlock()
 		return errors.New("dispatcher is already running")
 	}
-	ctx = log.WithModule(ctx, "dispatcher")
 	if err := d.markNodesUnknown(ctx); err != nil {
 		log.G(ctx).Errorf(`failed to move all nodes to "unknown" state: %v`, err)
 	}
@@ -310,8 +312,12 @@ func (d *Dispatcher) Stop() error {
 		d.mu.Unlock()
 		return errors.New("dispatcher is already stopped")
 	}
+
+	log := log.G(d.ctx).WithField("method", "(*Dispatcher).Stop")
+	log.Info("dispatcher stopping")
 	d.cancel()
 	d.mu.Unlock()
+
 	d.nodes.Clean()
 
 	d.processUpdatesLock.Lock()
@@ -361,13 +367,15 @@ func (d *Dispatcher) markNodesUnknown(ctx context.Context) error {
 				if node.Status.State == api.NodeStatus_DOWN {
 					nodeCopy := node
 					expireFunc := func() {
+						log.Infof("moving tasks to orphaned state for node: %s", nodeCopy.ID)
 						if err := d.moveTasksToOrphaned(nodeCopy.ID); err != nil {
-							log.WithError(err).Error(`failed to move all tasks to "ORPHANED" state`)
+							log.WithError(err).Errorf(`failed to move all tasks for node %s to "ORPHANED" state`, node.ID)
 						}
 
 						d.downNodes.Delete(nodeCopy.ID)
 					}
 
+					log.Infof(`node %s was found to be down when marking unknown on dispatcher start`, node.ID)
 					d.downNodes.Add(nodeCopy, expireFunc)
 					return nil
 				}
@@ -379,16 +387,16 @@ func (d *Dispatcher) markNodesUnknown(ctx context.Context) error {
 
 				expireFunc := func() {
 					log := log.WithField("node", nodeID)
-					log.Debug("heartbeat expiration for unknown node")
+					log.Info(`heartbeat expiration for node %s in state "unknown"`, nodeID)
 					if err := d.markNodeNotReady(nodeID, api.NodeStatus_DOWN, `heartbeat failure for node in "unknown" state`); err != nil {
 						log.WithError(err).Error(`failed deregistering node after heartbeat expiration for node in "unknown" state`)
 					}
 				}
 				if err := d.nodes.AddUnknown(node, expireFunc); err != nil {
-					return errors.Wrap(err, `adding node in "unknown" state to node store failed`)
+					return errors.Wrapf(err, `adding node %s in "unknown" state to node store failed`, nodeID)
 				}
 				if err := store.UpdateNode(tx, node); err != nil {
-					return errors.Wrap(err, "update failed")
+					return errors.Wrapf(err, "update for node %s failed", nodeID)
 				}
 				return nil
 			})
@@ -470,6 +478,7 @@ func nodeIPFromContext(ctx context.Context) (string, error) {
 
 // register is used for registration of node with particular dispatcher.
 func (d *Dispatcher) register(ctx context.Context, nodeID string, description *api.NodeDescription) (string, error) {
+	logLocal := log.G(ctx).WithField("method", "(*Dispatcher).register")
 	// prevent register until we're ready to accept it
 	dctx, err := d.isRunningLocked()
 	if err != nil {
@@ -491,7 +500,7 @@ func (d *Dispatcher) register(ctx context.Context, nodeID string, description *a
 
 	addr, err := nodeIPFromContext(ctx)
 	if err != nil {
-		log.G(ctx).WithError(err).Debug("failed to get remote node IP")
+		logLocal.WithError(err).Debug("failed to get remote node IP")
 	}
 
 	if err := d.markNodeReady(dctx, nodeID, description, addr); err != nil {
@@ -499,13 +508,14 @@ func (d *Dispatcher) register(ctx context.Context, nodeID string, description *a
 	}
 
 	expireFunc := func() {
-		log.G(ctx).Debug("heartbeat expiration")
+		log.G(ctx).Debug("heartbeat expiration for worker %s, setting worker status to NodeStatus_DOWN ", nodeID)
 		if err := d.markNodeNotReady(nodeID, api.NodeStatus_DOWN, "heartbeat failure"); err != nil {
 			log.G(ctx).WithError(err).Errorf("failed deregistering node after heartbeat expiration")
 		}
 	}
 
 	rn := d.nodes.Add(node, expireFunc)
+	logLocal.Infof("worker %s was successfully registered", nodeID)
 
 	// NOTE(stevvooe): We need be a little careful with re-registration. The
 	// current implementation just matches the node id and then gives away the
@@ -1029,6 +1039,8 @@ func (d *Dispatcher) moveTasksToOrphaned(nodeID string) error {
 
 // markNodeNotReady sets the node state to some state other than READY
 func (d *Dispatcher) markNodeNotReady(id string, state api.NodeStatus_State, message string) error {
+	logLocal := log.G(d.ctx).WithField("method", "(*Dispatcher).markNodeNotReady")
+
 	dctx, err := d.isRunningLocked()
 	if err != nil {
 		return err
@@ -1048,6 +1060,7 @@ func (d *Dispatcher) markNodeNotReady(id string, state api.NodeStatus_State, mes
 	}
 
 	expireFunc := func() {
+		log.G(dctx).Debugf(`worker timed-out %s in "down" state, moving all tasks to "ORPHANED" state`, id)
 		if err := d.moveTasksToOrphaned(id); err != nil {
 			log.G(dctx).WithError(err).Error(`failed to move all tasks to "ORPHANED" state`)
 		}
@@ -1056,6 +1069,7 @@ func (d *Dispatcher) markNodeNotReady(id string, state api.NodeStatus_State, mes
 	}
 
 	d.downNodes.Add(node, expireFunc)
+	logLocal.Debugf("added node %s to down nodes list", node.ID)
 
 	status := &api.NodeStatus{
 		State:   state,
@@ -1080,6 +1094,7 @@ func (d *Dispatcher) markNodeNotReady(id string, state api.NodeStatus_State, mes
 	if rn := d.nodes.Delete(id); rn == nil {
 		return errors.Errorf("node %s is not found in local storage", id)
 	}
+	logLocal.Debugf("deleted node %s from node store", node.ID)
 
 	return nil
 }
@@ -1094,6 +1109,8 @@ func (d *Dispatcher) Heartbeat(ctx context.Context, r *api.HeartbeatRequest) (*a
 	}
 
 	period, err := d.nodes.Heartbeat(nodeInfo.NodeID, r.SessionID)
+
+	log.G(ctx).WithField("method", "(*Dispatcher).Heartbeat").Debugf("received heartbeat from worker %v, expect next heartbeat in %v", nodeInfo, period)
 	return &api.HeartbeatResponse{Period: period}, err
 }
 
@@ -1206,6 +1223,7 @@ func (d *Dispatcher) Session(r *api.SessionRequest, stream api.Dispatcher_Sessio
 			}
 		}
 
+		log.Infof("dispatcher session dropped, marking node %s down", nodeID)
 		if err := d.markNodeNotReady(nodeID, api.NodeStatus_DISCONNECTED, "node is currently trying to find new manager"); err != nil {
 			log.WithError(err).Error("failed to remove node")
 		}