diff --git a/internal/pkg/coordinator/monitor.go b/internal/pkg/coordinator/monitor.go
index 66c934154..03019ac71 100644
--- a/internal/pkg/coordinator/monitor.go
+++ b/internal/pkg/coordinator/monitor.go
@@ -7,6 +7,7 @@ package coordinator
 import (
 	"context"
 	"errors"
+	"fmt"
 	"net"
 	"os"
 	"runtime"
@@ -132,7 +133,7 @@ func (m *monitorT) Run(ctx context.Context) (err error) {
 		case hits := <-s.Output():
 			err = m.handlePolicies(ctx, hits)
 			if err != nil {
-				return err
+				m.log.Warn().Err(err).Msgf("Encountered an error while policy leadership changes; continuing to retry.")
 			}
 		case <-mT.C:
 			m.calcMetadata()
@@ -140,7 +141,7 @@ func (m *monitorT) Run(ctx context.Context) (err error) {
 		case <-lT.C:
 			err = m.ensureLeadership(ctx)
 			if err != nil {
-				return err
+				m.log.Warn().Err(err).Msgf("Encountered an error while checking/assigning policy leaders; continuing to retry.")
 			}
 			lT.Reset(m.checkInterval)
 		case <-ctx.Done():
@@ -157,6 +158,7 @@ func (m *monitorT) handlePolicies(ctx context.Context, hits []es.HitT) error {
 		var policy model.Policy
 		err := hit.Unmarshal(&policy)
 		if err != nil {
+			m.log.Debug().Err(err).Msg("Failed to deserialize policy json")
 			return err
 		}
 		if policy.CoordinatorIdx != 0 {
@@ -170,6 +172,7 @@ func (m *monitorT) handlePolicies(ctx context.Context, hits []es.HitT) error {
 				// current leader send to its coordinator
 				err = p.cord.Update(ctx, policy)
 				if err != nil {
+					m.log.Info().Err(err).Msg("Failed to update policy leader")
 					return err
 				}
 			}
@@ -192,8 +195,9 @@ func (m *monitorT) handlePolicies(ctx context.Context, hits []es.HitT) error {
 func (m *monitorT) ensureLeadership(ctx context.Context) error {
 	m.log.Debug().Msg("ensuring leadership of policies")
 	err := dl.EnsureServer(ctx, m.bulker, m.version, m.agentMetadata, m.hostMetadata, dl.WithIndexName(m.serversIndex))
+
 	if err != nil {
-		return err
+		return fmt.Errorf("Failed to check server status on Elasticsearch (%s): %w", m.hostMetadata.Name, err)
 	}
 
 	// fetch current policies and leaders
@@ -204,7 +208,7 @@ func (m *monitorT) ensureLeadership(ctx context.Context) error {
 			m.log.Debug().Str("index", m.policiesIndex).Msg(es.ErrIndexNotFound.Error())
 			return nil
 		}
-		return err
+		return fmt.Errorf("Encountered error while querying policies: %w", err)
 	}
 	if len(policies) > 0 {
 		ids := make([]string, len(policies))
@@ -214,7 +218,7 @@ func (m *monitorT) ensureLeadership(ctx context.Context) error {
 		leaders, err = dl.SearchPolicyLeaders(ctx, m.bulker, ids, dl.WithIndexName(m.leadersIndex))
 		if err != nil {
 			if !errors.Is(err, es.ErrIndexNotFound) {
-				return err
+				return fmt.Errorf("Encountered error while fetching policy leaders: %w", err)
 			}
 		}
 	}