diff --git a/CHANGELOG.next.asciidoc b/CHANGELOG.next.asciidoc
index 7d500cf8f53..0e1a8adb79c 100644
--- a/CHANGELOG.next.asciidoc
+++ b/CHANGELOG.next.asciidoc
@@ -208,3 +208,5 @@
 - Add `lumberjack` input type to the Filebeat spec. {pull}[959]
 - Add support for hints' based autodiscovery in kubernetes provider. {pull}[698]
 - Improve logging during upgrades. {pull}[1287]
+- Added status message to CheckinRequest {pull}[1369]
+- Improve logging of Fleet checkins errors. {pull}[1477]
diff --git a/changelog/fragments/1665517984-improve-checkin-error-logging.yaml b/changelog/fragments/1665517984-improve-checkin-error-logging.yaml
new file mode 100644
index 00000000000..7bf2777d9d5
--- /dev/null
+++ b/changelog/fragments/1665517984-improve-checkin-error-logging.yaml
@@ -0,0 +1,5 @@
+kind: enhancement
+summary: Improve logging of Fleet check-in errors.
+description: Improve logging of Fleet check-in errors and only report the local state as degraded after two consecutive failed check-ins.
+pr: 1477
+issue: 1154
diff --git a/internal/pkg/agent/application/gateway/fleet/fleet_gateway.go b/internal/pkg/agent/application/gateway/fleet/fleet_gateway.go
index b88a0cafee0..f90d94b396d 100644
--- a/internal/pkg/agent/application/gateway/fleet/fleet_gateway.go
+++ b/internal/pkg/agent/application/gateway/fleet/fleet_gateway.go
@@ -173,7 +173,7 @@ func (f *fleetGateway) worker() {
 			// Execute the checkin call and for any errors returned by the fleet-server API
 			// the function will retry to communicate with fleet-server with an exponential delay and some
 			// jitter to help better distribute the load from a fleet of agents.
-			resp, err := f.doExecute()
+			resp, err := f.executeCheckinWithRetries()
 			if err != nil {
 				continue
 			}
@@ -274,21 +274,34 @@ func (f *fleetGateway) gatherQueuedActions(ts time.Time) (queued, expired []flee
 	return queued, expired
 }
 
-func (f *fleetGateway) doExecute() (*fleetapi.CheckinResponse, error) {
+func (f *fleetGateway) executeCheckinWithRetries() (*fleetapi.CheckinResponse, error) {
 	f.backoff.Reset()
 
 	// Guard if the context is stopped by a out of bound call,
 	// this mean we are rebooting to change the log level or the system is shutting us down.
 	for f.bgContext.Err() == nil {
 		f.log.Debugf("Checkin started")
-		resp, err := f.execute(f.bgContext)
+		resp, took, err := f.executeCheckin(f.bgContext)
 		if err != nil {
 			f.checkinFailCounter++
-			f.log.Errorf("Could not communicate with fleet-server checkin API will retry, error: %s", err)
+
+			// Report the first two failures at warn level as they may be recoverable with retries.
+			if f.checkinFailCounter <= 2 {
+				f.log.Warnw("Possible transient error during checkin with fleet-server, retrying",
+					"error.message", err, "request_duration_ns", took, "failed_checkins", f.checkinFailCounter,
+					"retry_after_ns", f.backoff.NextWait())
+			} else {
+				// Only update the local status after repeated failures: https://github.com/elastic/elastic-agent/issues/1148
+				f.localReporter.Update(state.Degraded, fmt.Sprintf("checkin failed: %v", err), nil)
+				f.log.Errorw("Cannot checkin in with fleet-server, retrying",
+					"error.message", err, "request_duration_ns", took, "failed_checkins", f.checkinFailCounter,
+					"retry_after_ns", f.backoff.NextWait())
+			}
+
 			if !f.backoff.Wait() {
 				// Something bad has happened and we log it and we should update our current state.
 				err := errors.New(
-					"execute retry loop was stopped",
+					"checkin retry loop was stopped",
 					errors.TypeNetwork,
 					errors.M(errors.MetaKeyURI, f.client.URI()),
 				)
@@ -297,10 +310,6 @@ func (f *fleetGateway) doExecute() (*fleetapi.CheckinResponse, error) {
 				f.localReporter.Update(state.Failed, err.Error(), nil)
 				return nil, err
 			}
-			if f.checkinFailCounter > 1 {
-				f.localReporter.Update(state.Degraded, fmt.Sprintf("checkin failed: %v", err), nil)
-				f.log.Errorf("checkin number %d failed: %s", f.checkinFailCounter, err.Error())
-			}
 			continue
 		}
 
@@ -319,7 +328,7 @@ func (f *fleetGateway) doExecute() (*fleetapi.CheckinResponse, error) {
 	return nil, f.bgContext.Err()
 }
 
-func (f *fleetGateway) execute(ctx context.Context) (*fleetapi.CheckinResponse, error) {
+func (f *fleetGateway) executeCheckin(ctx context.Context) (*fleetapi.CheckinResponse, time.Duration, error) {
 	ecsMeta, err := info.Metadata()
 	if err != nil {
 		f.log.Error(errors.New("failed to load metadata", err))
@@ -339,7 +348,7 @@ func (f *fleetGateway) execute(ctx context.Context) (*fleetapi.CheckinResponse,
 		Status:   f.statusController.StatusString(),
 	}
 
-	resp, err := cmd.Execute(ctx, req)
+	resp, took, err := cmd.Execute(ctx, req)
 	if isUnauth(err) {
 		f.unauthCounter++
 
@@ -347,15 +356,15 @@ func (f *fleetGateway) execute(ctx context.Context) (*fleetapi.CheckinResponse,
 			f.log.Warnf("received an invalid api key error '%d' times. Starting to unenroll the elastic agent.", f.unauthCounter)
 			return &fleetapi.CheckinResponse{
 				Actions: []fleetapi.Action{&fleetapi.ActionUnenroll{ActionID: "", ActionType: "UNENROLL", IsDetected: true}},
-			}, nil
+			}, took, nil
 		}
 
-		return nil, err
+		return nil, took, err
 	}
 
 	f.unauthCounter = 0
 	if err != nil {
-		return nil, err
+		return nil, took, err
 	}
 
 	// Save the latest ackToken
@@ -367,7 +376,7 @@ func (f *fleetGateway) execute(ctx context.Context) (*fleetapi.CheckinResponse,
 		}
 	}
 
-	return resp, nil
+	return resp, took, nil
 }
 
 // shouldUnenroll checks if the max number of trying an invalid key is reached
diff --git a/internal/pkg/agent/application/gateway/fleet/fleet_gateway_test.go b/internal/pkg/agent/application/gateway/fleet/fleet_gateway_test.go
index 2d691185c1c..722bd792f95 100644
--- a/internal/pkg/agent/application/gateway/fleet/fleet_gateway_test.go
+++ b/internal/pkg/agent/application/gateway/fleet/fleet_gateway_test.go
@@ -21,6 +21,7 @@ import (
 	"github.com/stretchr/testify/mock"
 	"github.com/stretchr/testify/require"
 
+	"github.com/elastic/elastic-agent-libs/logp"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/gateway"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/paths"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/storage"
@@ -692,7 +693,7 @@ func TestRetriesOnFailures(t *testing.T) {
 		scheduler := scheduler.NewStepper()
 		client := newTestingClient()
 		dispatcher := newTestingDispatcher()
-		log, _ := logger.New("fleet_gateway", false)
+		log := newInfoLogger(t, "fleet_gateway")
 		ctx, cancel := context.WithCancel(context.Background())
 		defer cancel()
 
@@ -705,8 +706,8 @@ func TestRetriesOnFailures(t *testing.T) {
 		queue.On("Actions").Return([]fleetapi.Action{})
 
 		localReporter := &testutils.MockReporter{}
-		localReporter.On("Update", state.Degraded, mock.Anything, mock.Anything).Times(2)
-		localReporter.On("Update", mock.Anything, mock.Anything, mock.Anything).Maybe()
+		// The local state should only be reported as degraded after two consecutive failures.
+		localReporter.On("Update", state.Degraded, mock.Anything, mock.Anything).Once()
 		localReporter.On("Unregister").Maybe()
 
 		fleetReporter := &testutils.MockReporter{}
@@ -812,3 +813,16 @@ type testAgentInfo struct{}
 func (testAgentInfo) AgentID() string { return "agent-secret" }
 
 type request struct{}
+
+func newInfoLogger(t *testing.T, name string) *logger.Logger {
+	t.Helper()
+
+	loggerCfg := logger.DefaultLoggingConfig()
+	loggerCfg.Level = logp.InfoLevel
+	loggerCfg.ToFiles = false
+	loggerCfg.ToStderr = true
+
+	log, err := logger.NewFromConfig("", loggerCfg, false)
+	require.NoError(t, err)
+	return log
+}
diff --git a/internal/pkg/core/backoff/backoff.go b/internal/pkg/core/backoff/backoff.go
index 06723e7db9a..c97eaae199d 100644
--- a/internal/pkg/core/backoff/backoff.go
+++ b/internal/pkg/core/backoff/backoff.go
@@ -4,11 +4,16 @@
 
 package backoff
 
+import "time"
+
 // Backoff defines the interface for backoff strategies.
 type Backoff interface {
 	// Wait blocks for a duration of time governed by the backoff strategy.
 	Wait() bool
 
+	// NextWait returns the duration of the next call to Wait().
+	NextWait() time.Duration
+
 	// Reset resets the backoff duration to an initial value governed by the backoff strategy.
 	Reset()
 }
diff --git a/internal/pkg/core/backoff/backoff_test.go b/internal/pkg/core/backoff/backoff_test.go
index 88498ff5a58..12332eb15f2 100644
--- a/internal/pkg/core/backoff/backoff_test.go
+++ b/internal/pkg/core/backoff/backoff_test.go
@@ -14,14 +14,9 @@ import (
 
 type factory func(<-chan struct{}) Backoff
 
-func TestBackoff(t *testing.T) {
-	t.Run("test close channel", testCloseChannel)
-	t.Run("test unblock after some time", testUnblockAfterInit)
-}
-
-func testCloseChannel(t *testing.T) {
-	init := 2 * time.Second
-	max := 5 * time.Minute
+func TestCloseChannel(t *testing.T) {
+	init := 2 * time.Millisecond
+	max := 5 * time.Second
 
 	tests := map[string]factory{
 		"ExpBackoff": func(done <-chan struct{}) Backoff {
@@ -42,9 +37,9 @@ func testCloseChannel(t *testing.T) {
 	}
 }
 
-func testUnblockAfterInit(t *testing.T) {
-	init := 1 * time.Second
-	max := 5 * time.Minute
+func TestUnblockAfterInit(t *testing.T) {
+	init := 1 * time.Millisecond
+	max := 5 * time.Second
 
 	tests := map[string]factory{
 		"ExpBackoff": func(done <-chan struct{}) Backoff {
@@ -68,3 +63,36 @@ func testUnblockAfterInit(t *testing.T) {
 		})
 	}
 }
+
+func TestNextWait(t *testing.T) {
+	init := time.Millisecond
+	max := 5 * time.Second
+
+	tests := map[string]factory{
+		"ExpBackoff": func(done <-chan struct{}) Backoff {
+			return NewExpBackoff(done, init, max)
+		},
+		"EqualJitterBackoff": func(done <-chan struct{}) Backoff {
+			return NewEqualJitterBackoff(done, init, max)
+		},
+	}
+
+	for name, f := range tests {
+		t.Run(name, func(t *testing.T) {
+			c := make(chan struct{})
+			b := f(c)
+
+			startWait := b.NextWait()
+			assert.Equal(t, startWait, b.NextWait(), "next wait not stable")
+
+			startedAt := time.Now()
+			b.Wait()
+			waitDuration := time.Now().Sub(startedAt)
+			nextWait := b.NextWait()
+
+			t.Logf("actualWait: %s startWait: %s nextWait: %s", waitDuration, startWait, nextWait)
+			assert.Less(t, startWait, nextWait, "wait value did not increase")
+			assert.GreaterOrEqual(t, waitDuration, startWait, "next wait duration <= actual wait duration")
+		})
+	}
+}
diff --git a/internal/pkg/core/backoff/equal_jitter.go b/internal/pkg/core/backoff/equal_jitter.go
index d87077397cd..671201f5892 100644
--- a/internal/pkg/core/backoff/equal_jitter.go
+++ b/internal/pkg/core/backoff/equal_jitter.go
@@ -16,8 +16,9 @@ type EqualJitterBackoff struct {
 	duration time.Duration
 	done     <-chan struct{}
 
-	init time.Duration
-	max  time.Duration
+	init     time.Duration
+	max      time.Duration
+	nextRand time.Duration
 
 	last time.Time
 }
@@ -29,6 +30,7 @@ func NewEqualJitterBackoff(done <-chan struct{}, init, max time.Duration) Backof
 		done:     done,
 		init:     init,
 		max:      max,
+		nextRand: time.Duration(rand.Int63n(int64(init))), //nolint:gosec
 	}
 }
 
@@ -38,13 +40,18 @@ func (b *EqualJitterBackoff) Reset() {
 	b.duration = b.init * 2
 }
 
+func (b *EqualJitterBackoff) NextWait() time.Duration {
+	// Make sure we have always some minimal back off and jitter.
+	temp := b.duration / 2
+	return temp + b.nextRand
+}
+
 // Wait block until either the timer is completed or channel is done.
 func (b *EqualJitterBackoff) Wait() bool {
-	// Make sure we have always some minimal back off and jitter.
-	temp := int64(b.duration / 2)
-	backoff := time.Duration(temp + rand.Int63n(temp))
+	backoff := b.NextWait()
 
 	// increase duration for next wait.
+	b.nextRand = time.Duration(rand.Int63n(int64(b.duration)))
 	b.duration *= 2
 	if b.duration > b.max {
 		b.duration = b.max
diff --git a/internal/pkg/core/backoff/exponential.go b/internal/pkg/core/backoff/exponential.go
index 81224b95eb5..51b5b4e0cb5 100644
--- a/internal/pkg/core/backoff/exponential.go
+++ b/internal/pkg/core/backoff/exponential.go
@@ -36,18 +36,23 @@ func (b *ExpBackoff) Reset() {
 	b.duration = b.init
 }
 
+func (b *ExpBackoff) NextWait() time.Duration {
+	nextWait := b.duration
+	nextWait *= 2
+	if nextWait > b.max {
+		nextWait = b.max
+	}
+	return nextWait
+}
+
 // Wait block until either the timer is completed or channel is done.
 func (b *ExpBackoff) Wait() bool {
-	backoff := b.duration
-	b.duration *= 2
-	if b.duration > b.max {
-		b.duration = b.max
-	}
+	b.duration = b.NextWait()
 
 	select {
 	case <-b.done:
 		return false
-	case <-time.After(backoff):
+	case <-time.After(b.duration):
 		b.last = time.Now()
 		return true
 	}
diff --git a/internal/pkg/fleetapi/checkin_cmd.go b/internal/pkg/fleetapi/checkin_cmd.go
index e225aababb9..89faf0aba2a 100644
--- a/internal/pkg/fleetapi/checkin_cmd.go
+++ b/internal/pkg/fleetapi/checkin_cmd.go
@@ -77,23 +77,26 @@ func NewCheckinCmd(info agentInfo, client client.Sender) *CheckinCmd {
 	}
 }
 
-// Execute enroll the Agent in the Fleet Server.
-func (e *CheckinCmd) Execute(ctx context.Context, r *CheckinRequest) (*CheckinResponse, error) {
+// Execute enroll the Agent in the Fleet Server. Returns the decoded check in response, a duration indicating
+// how long the request took, and an error.
+func (e *CheckinCmd) Execute(ctx context.Context, r *CheckinRequest) (*CheckinResponse, time.Duration, error) {
 	if err := r.Validate(); err != nil {
-		return nil, err
+		return nil, 0, err
 	}
 
 	b, err := json.Marshal(r)
 	if err != nil {
-		return nil, errors.New(err,
+		return nil, 0, errors.New(err,
 			"fail to encode the checkin request",
 			errors.TypeUnexpected)
 	}
 
 	cp := fmt.Sprintf(checkingPath, e.info.AgentID())
+	sendStart := time.Now()
 	resp, err := e.client.Send(ctx, "POST", cp, nil, nil, bytes.NewBuffer(b))
+	sendDuration := time.Now().Sub(sendStart)
 	if err != nil {
-		return nil, errors.New(err,
+		return nil, sendDuration, errors.New(err,
 			"fail to checkin to fleet-server",
 			errors.TypeNetwork,
 			errors.M(errors.MetaKeyURI, cp))
@@ -101,26 +104,26 @@ func (e *CheckinCmd) Execute(ctx context.Context, r *CheckinRequest) (*CheckinRe
 	defer resp.Body.Close()
 
 	if resp.StatusCode != http.StatusOK {
-		return nil, client.ExtractError(resp.Body)
+		return nil, sendDuration, client.ExtractError(resp.Body)
 	}
 
 	rs, err := ioutil.ReadAll(resp.Body)
 	if err != nil {
-		return nil, errors.New(err, "failed to read checkin response")
+		return nil, sendDuration, errors.New(err, "failed to read checkin response")
 	}
 
 	checkinResponse := &CheckinResponse{}
 	decoder := json.NewDecoder(bytes.NewReader(rs))
 	if err := decoder.Decode(checkinResponse); err != nil {
-		return nil, errors.New(err,
+		return nil, sendDuration, errors.New(err,
 			"fail to decode checkin response",
 			errors.TypeNetwork,
 			errors.M(errors.MetaKeyURI, cp))
 	}
 
 	if err := checkinResponse.Validate(); err != nil {
-		return nil, err
+		return nil, sendDuration, err
 	}
 
-	return checkinResponse, nil
+	return checkinResponse, sendDuration, nil
 }
diff --git a/internal/pkg/fleetapi/checkin_cmd_test.go b/internal/pkg/fleetapi/checkin_cmd_test.go
index 2d9aef2741a..56726bb5559 100644
--- a/internal/pkg/fleetapi/checkin_cmd_test.go
+++ b/internal/pkg/fleetapi/checkin_cmd_test.go
@@ -11,6 +11,7 @@ import (
 	"io/ioutil"
 	"net/http"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -25,6 +26,7 @@ func (*agentinfo) AgentID() string { return "id" }
 
 func TestCheckin(t *testing.T) {
 	const withAPIKey = "secret"
+	const requestDelay = time.Millisecond
 	ctx := context.Background()
 	agentInfo := &agentinfo{}
 
@@ -39,6 +41,8 @@ func TestCheckin(t *testing.T) {
 			mux.HandleFunc(path, authHandler(func(w http.ResponseWriter, r *http.Request) {
 				w.WriteHeader(http.StatusInternalServerError)
 				fmt.Fprint(w, raw)
+				// Introduce a small delay to test the request time measurment.
+				time.Sleep(requestDelay)
 			}, withAPIKey))
 			return mux
 		}, withAPIKey,
@@ -47,8 +51,10 @@ func TestCheckin(t *testing.T) {
 
 			request := CheckinRequest{}
 
-			_, err := cmd.Execute(ctx, &request)
+			_, took, err := cmd.Execute(ctx, &request)
 			require.Error(t, err)
+			// Ensure the request took at least as long as the artificial delay.
+			require.GreaterOrEqual(t, took, requestDelay)
 		},
 	))
 
@@ -96,7 +102,7 @@ func TestCheckin(t *testing.T) {
 
 			request := CheckinRequest{}
 
-			r, err := cmd.Execute(ctx, &request)
+			r, _, err := cmd.Execute(ctx, &request)
 			require.NoError(t, err)
 
 			require.Equal(t, 1, len(r.Actions))
@@ -157,7 +163,7 @@ func TestCheckin(t *testing.T) {
 
 			request := CheckinRequest{}
 
-			r, err := cmd.Execute(ctx, &request)
+			r, _, err := cmd.Execute(ctx, &request)
 			require.NoError(t, err)
 
 			require.Equal(t, 2, len(r.Actions))
@@ -173,7 +179,7 @@ func TestCheckin(t *testing.T) {
 		},
 	))
 
-	t.Run("When we receive no action", withServerWithAuthClient(
+	t.Run("When we receive no action with delay", withServerWithAuthClient(
 		func(t *testing.T) *http.ServeMux {
 			raw := `{ "actions": [] }`
 			mux := http.NewServeMux()
@@ -189,7 +195,7 @@ func TestCheckin(t *testing.T) {
 
 			request := CheckinRequest{}
 
-			r, err := cmd.Execute(ctx, &request)
+			r, _, err := cmd.Execute(ctx, &request)
 			require.NoError(t, err)
 
 			require.Equal(t, 0, len(r.Actions))
@@ -223,7 +229,7 @@ func TestCheckin(t *testing.T) {
 
 			request := CheckinRequest{Metadata: testMetadata()}
 
-			r, err := cmd.Execute(ctx, &request)
+			r, _, err := cmd.Execute(ctx, &request)
 			require.NoError(t, err)
 
 			require.Equal(t, 0, len(r.Actions))
@@ -257,7 +263,7 @@ func TestCheckin(t *testing.T) {
 
 			request := CheckinRequest{}
 
-			r, err := cmd.Execute(ctx, &request)
+			r, _, err := cmd.Execute(ctx, &request)
 			require.NoError(t, err)
 
 			require.Equal(t, 0, len(r.Actions))