diff --git a/changelog/fragments/1740760469-Clear-agent-upgrade-attempts-when-upgrade-complete.yaml b/changelog/fragments/1740760469-Clear-agent-upgrade-attempts-when-upgrade-complete.yaml
new file mode 100644
index 0000000000..a57476baa6
--- /dev/null
+++ b/changelog/fragments/1740760469-Clear-agent-upgrade-attempts-when-upgrade-complete.yaml
@@ -0,0 +1,34 @@
+# Kind can be one of:
+# - breaking-change: a change to previously-documented behavior
+# - deprecation: functionality that is being removed in a later release
+# - bug-fix: fixes a problem in a previous version
+# - enhancement: extends functionality but does not break or fix existing behavior
+# - feature: new functionality
+# - known-issue: problems that we are aware of in a given version
+# - security: impacts on the security of a product or a user’s deployment.
+# - upgrade: important information for someone upgrading from a prior version
+# - other: does not fit into any of the other categories
+kind: enhancement
+
+# Change summary; a 80ish characters long description of the change.
+summary: Clear agent.upgrade_attempts when upgrade is complete.
+
+# Long description; in case the summary is not enough to describe the change
+# this field accommodate a description without length limits.
+# NOTE: This field will be rendered only for breaking-change and known-issue kinds at the moment.
+description: |
+  The new AutomaticAgentUpgradeTask Kibana task sets the upgrade_attempts property in agents it upgrades.
+  This property is used to track upgrade retries and should therefore be cleared when the upgrade is complete.
+
+# Affected component; usually one of "elastic-agent", "fleet-server", "filebeat", "metricbeat", "auditbeat", "all", etc.
+component: fleet-server
+
+# PR URL; optional; the PR number that added the changeset.
+# If not present is automatically filled by the tooling finding the PR where this changelog fragment has been added.
+# NOTE: the tooling supports backports, so it's able to fill the original PR number instead of the backport PR number.
+# Please provide it if you are adding a fragment for a different PR.
+pr: https://github.com/elastic/fleet-server/pull/4528
+
+# Issue URL; optional; the GitHub issue related to this changeset (either closes or is part of).
+# If not present is automatically filled by the tooling with the issue linked to the PR number.
+# issue: 
diff --git a/internal/pkg/api/handleCheckin.go b/internal/pkg/api/handleCheckin.go
index 38cd78836a..6bbe9f877e 100644
--- a/internal/pkg/api/handleCheckin.go
+++ b/internal/pkg/api/handleCheckin.go
@@ -219,7 +219,7 @@ func (ct *CheckinT) validateRequest(zlog zerolog.Logger, w http.ResponseWriter,
 		}
 
 		wTime := pollDuration + time.Minute
-		rc := http.NewResponseController(w) //nolint:bodyclose // we are working with a ResponseWriter not a Respons
+		rc := http.NewResponseController(w)
 		if err := rc.SetWriteDeadline(start.Add(wTime)); err != nil {
 			zlog.Warn().Err(err).Time("write_deadline", start.Add(wTime)).Msg("Unable to set checkin write deadline.")
 		} else {
@@ -398,6 +398,26 @@ func (ct *CheckinT) ProcessRequest(zlog zerolog.Logger, w http.ResponseWriter, r
 	return ct.writeResponse(zlog, w, r, agent, resp)
 }
 
+func (ct *CheckinT) verifyActionExists(vCtx context.Context, vSpan *apm.Span, agent *model.Agent, details *UpgradeDetails) (*model.Action, error) {
+	action, ok := ct.cache.GetAction(details.ActionId)
+	if !ok {
+		actions, err := dl.FindAction(vCtx, ct.bulker, details.ActionId)
+		if err != nil {
+			vSpan.End()
+			return nil, fmt.Errorf("unable to find upgrade_details action: %w", err)
+		}
+		if len(actions) == 0 {
+			vSpan.End()
+			zerolog.Ctx(vCtx).Warn().Msgf("upgrade_details no action for id %q found (agent id %q)", details.ActionId, agent.Agent.ID)
+			return nil, nil
+		}
+		action = actions[0]
+		ct.cache.SetAction(action)
+	}
+	vSpan.End()
+	return &action, nil
+}
+
 // processUpgradeDetails will verify and set the upgrade_details section of an agent document based on checkin value.
 // if the agent doc and checkin details are both nil the method is a nop
 // if the checkin upgrade_details is nil but there was a previous value in the agent doc, fleet-server treats it as a successful upgrade
@@ -412,24 +432,14 @@ func (ct *CheckinT) processUpgradeDetails(ctx context.Context, agent *model.Agen
 	}
 	// update docs with in progress details
 
-	// verify action exists
 	vSpan, vCtx := apm.StartSpan(ctx, "Check update action", "validate")
-	action, ok := ct.cache.GetAction(details.ActionId)
-	if !ok {
-		actions, err := dl.FindAction(vCtx, ct.bulker, details.ActionId)
-		if err != nil {
-			vSpan.End()
-			return fmt.Errorf("unable to find upgrade_details action: %w", err)
-		}
-		if len(actions) == 0 {
-			vSpan.End()
-			zerolog.Ctx(vCtx).Warn().Msgf("upgrade_details no action for id %q found (agent id %q)", details.ActionId, agent.Agent.ID)
-			return nil
-		}
-		action = actions[0]
-		ct.cache.SetAction(action)
+	action, err := ct.verifyActionExists(ctx, vSpan, agent, details)
+	if err != nil {
+		return err
+	}
+	if action == nil {
+		return nil
 	}
-	vSpan.End()
 
 	// link action with APM spans
 	var links []apm.SpanLink
@@ -500,6 +510,10 @@ func (ct *CheckinT) processUpgradeDetails(ctx context.Context, agent *model.Agen
 	doc := bulk.UpdateFields{
 		dl.FieldUpgradeDetails: details,
 	}
+	if agent.UpgradeAttempts != nil && details.State == UpgradeDetailsStateUPGWATCHING {
+		doc[dl.FieldUpgradeAttempts] = nil
+	}
+
 	body, err := doc.Marshal()
 	if err != nil {
 		return err
diff --git a/internal/pkg/api/handleCheckin_test.go b/internal/pkg/api/handleCheckin_test.go
index cc5652f2da..da0e52d4fa 100644
--- a/internal/pkg/api/handleCheckin_test.go
+++ b/internal/pkg/api/handleCheckin_test.go
@@ -17,6 +17,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/elastic/fleet-server/v7/internal/pkg/bulk"
 	"github.com/elastic/fleet-server/v7/internal/pkg/cache"
 	"github.com/elastic/fleet-server/v7/internal/pkg/checkin"
 	"github.com/elastic/fleet-server/v7/internal/pkg/config"
@@ -312,6 +313,17 @@ func TestResolveSeqNo(t *testing.T) {
 
 func TestProcessUpgradeDetails(t *testing.T) {
 	esd := model.ESDocument{Id: "doc-ID"}
+	doc := bulk.UpdateFields{
+		dl.FieldUpgradeDetails: &UpgradeDetails{
+			ActionId: "test-action",
+			State:    UpgradeDetailsStateUPGWATCHING,
+		},
+		dl.FieldUpgradeAttempts: nil,
+	}
+	body, err := doc.Marshal()
+	if err != nil {
+		t.Fatalf("marshal error: %v", err)
+	}
 	tests := []struct {
 		name    string
 		agent   *model.Agent
@@ -625,6 +637,24 @@ func TestProcessUpgradeDetails(t *testing.T) {
 				return mCache
 			},
 			err: ErrInvalidUpgradeMetadata,
+		}, {
+			name:  "clear upgrade attempts when watching",
+			agent: &model.Agent{ESDocument: esd, Agent: &model.AgentMetadata{ID: "test-agent"}, UpgradeAttempts: make([]string, 0)},
+			details: &UpgradeDetails{
+				ActionId: "test-action",
+				State:    UpgradeDetailsStateUPGWATCHING,
+			},
+			bulk: func() *ftesting.MockBulk {
+				mBulk := ftesting.NewMockBulk()
+				mBulk.On("Update", mock.Anything, dl.FleetAgents, "doc-ID", body, mock.Anything, mock.Anything).Return(nil)
+				return mBulk
+			},
+			cache: func() *testcache.MockCache {
+				mCache := testcache.NewMockCache()
+				mCache.On("GetAction", "test-action").Return(model.Action{}, true)
+				return mCache
+			},
+			err: nil,
 		}}
 
 	for _, tc := range tests {
diff --git a/internal/pkg/dl/constants.go b/internal/pkg/dl/constants.go
index 73d382789f..9c191955aa 100644
--- a/internal/pkg/dl/constants.go
+++ b/internal/pkg/dl/constants.go
@@ -54,6 +54,7 @@ const (
 	FieldUpgradeStartedAt = "upgrade_started_at"
 	FieldUpgradeStatus    = "upgrade_status"
 	FieldUpgradeDetails   = "upgrade_details"
+	FieldUpgradeAttempts  = "upgrade_attempts"
 
 	FieldAuditUnenrolledTime   = "audit_unenrolled_time"
 	FieldAuditUnenrolledReason = "audit_unenrolled_reason"
diff --git a/internal/pkg/model/schema.go b/internal/pkg/model/schema.go
index 7991bd3aac..11ffac6a94 100644
--- a/internal/pkg/model/schema.go
+++ b/internal/pkg/model/schema.go
@@ -216,6 +216,9 @@ type Agent struct {
 	// Date/time the Elastic Agent was last updated
 	UpdatedAt string `json:"updated_at,omitempty"`
 
+	// List of timestamps of attempts of Elastic Agent automatic upgrades
+	UpgradeAttempts []string `json:"upgrade_attempts,omitempty"`
+
 	// Additional upgrade status details.
 	UpgradeDetails *UpgradeDetails `json:"upgrade_details,omitempty"`
 
diff --git a/model/schema.json b/model/schema.json
index 6fb03c87cb..8e19b7b7f9 100644
--- a/model/schema.json
+++ b/model/schema.json
@@ -686,6 +686,13 @@
           "description": "Additional upgrade status details.",
           "type": "object"
         },
+        "upgrade_attempts": {
+          "description": "List of timestamps of attempts of Elastic Agent automatic upgrades",
+          "type": "array",
+          "items": {
+            "type": "string"
+          }
+        },
         "replace_token": {
           "description": "hash of token provided during enrollment that allows replacement by another enrollment with same ID",
           "type": "string"