diff --git a/conf/defaults.ini b/conf/defaults.ini
index f9e230c580e..aa746872133 100644
--- a/conf/defaults.ini
+++ b/conf/defaults.ini
@@ -1387,6 +1387,12 @@ loki_basic_auth_password =
 # Optional max query length for queries sent to Loki. Default is 721h which matches the default Loki value.
 loki_max_query_length = 721h
 
+# For "loki" only.
+# Maximum size in bytes for queries sent to Loki. This limit is applied to user provided filters as well as system defined ones, e.g. applied by access control.
+# If filter exceeds the limit, API returns error with code "alerting.state-history.loki.requestTooLong".
+# Default is 64kb
+loki_max_query_size = 65536
+
 [unified_alerting.state_history.external_labels]
 # Optional extra labels to attach to outbound state history records or log streams.
 # Any number of label key-value-pairs can be provided.
diff --git a/conf/sample.ini b/conf/sample.ini
index 5257c046add..e261822eb57 100644
--- a/conf/sample.ini
+++ b/conf/sample.ini
@@ -1379,6 +1379,12 @@ disabled_labels =
 # Optional max query length for queries sent to Loki. Default is 721h which matches the default Loki value.
 ; loki_max_query_length = 360h
 
+# For "loki" only.
+# Maximum size in bytes for queries sent to Loki. This limit is applied to user provided filters as well as system defined ones, e.g. applied by access control.
+# If filter exceeds the limit, API returns error with code "alerting.state-history.loki.requestTooLong".
+# Default is 64kb
+;loki_max_query_size = 65536
+
 [unified_alerting.state_history.external_labels]
 # Optional extra labels to attach to outbound state history records or log streams.
 # Any number of label key-value-pairs can be provided.
diff --git a/pkg/services/annotations/annotationsimpl/loki/historian_store.go b/pkg/services/annotations/annotationsimpl/loki/historian_store.go
index b4e411b4a54..3fd0d7ca907 100644
--- a/pkg/services/annotations/annotationsimpl/loki/historian_store.go
+++ b/pkg/services/annotations/annotationsimpl/loki/historian_store.go
@@ -45,6 +45,7 @@ var (
 
 type lokiQueryClient interface {
 	RangeQuery(ctx context.Context, query string, start, end, limit int64) (historian.QueryRes, error)
+	MaxQuerySize() int
 }
 
 // LokiHistorianStore is a read store that queries Loki for alert state history.
@@ -98,8 +99,12 @@ func (r *LokiHistorianStore) Get(ctx context.Context, query *annotations.ItemQue
 		}
 	}
 
-	logQL, err := historian.BuildLogQuery(buildHistoryQuery(query, accessResources.Dashboards, rule.UID))
+	logQL, err := historian.BuildLogQuery(buildHistoryQuery(query, accessResources.Dashboards, rule.UID), r.client.MaxQuerySize())
 	if err != nil {
+		grafanaErr := errutil.Error{}
+		if errors.As(err, &grafanaErr) {
+			return make([]*annotations.ItemDTO, 0), err
+		}
 		return make([]*annotations.ItemDTO, 0), ErrLokiStoreInternal.Errorf("failed to build loki query: %w", err)
 	}
 
diff --git a/pkg/services/annotations/annotationsimpl/loki/historian_store_test.go b/pkg/services/annotations/annotationsimpl/loki/historian_store_test.go
index 5202952cda9..ff08aaee047 100644
--- a/pkg/services/annotations/annotationsimpl/loki/historian_store_test.go
+++ b/pkg/services/annotations/annotationsimpl/loki/historian_store_test.go
@@ -778,6 +778,7 @@ func NewFakeLokiClient() *FakeLokiClient {
 			ReadPathURL:    url,
 			Encoder:        historian.JsonEncoder{},
 			MaxQueryLength: 721 * time.Hour,
+			MaxQuerySize:   65536,
 		},
 		metrics: metrics,
 		log:     log.New("ngalert.state.historian", "backend", "loki"),
@@ -812,6 +813,10 @@ func (c *FakeLokiClient) RangeQuery(ctx context.Context, query string, from, to,
 	return res, nil
 }
 
+func (c *FakeLokiClient) MaxQuerySize() int {
+	return c.cfg.MaxQuerySize
+}
+
 func TestUseStore(t *testing.T) {
 	t.Run("false if state history disabled", func(t *testing.T) {
 		cfg := setting.UnifiedAlertingStateHistorySettings{
diff --git a/pkg/services/ngalert/state/historian/loki.go b/pkg/services/ngalert/state/historian/loki.go
index fd163a3a806..fefbe48e462 100644
--- a/pkg/services/ngalert/state/historian/loki.go
+++ b/pkg/services/ngalert/state/historian/loki.go
@@ -12,6 +12,7 @@ import (
 	"github.com/grafana/grafana-plugin-sdk-go/data"
 	"go.opentelemetry.io/otel/trace"
 
+	"github.com/grafana/grafana/pkg/apimachinery/errutil"
 	"github.com/grafana/grafana/pkg/components/simplejson"
 	"github.com/grafana/grafana/pkg/infra/log"
 	"github.com/grafana/grafana/pkg/infra/tracing"
@@ -41,10 +42,30 @@ const (
 
 const defaultQueryRange = 6 * time.Hour
 
+var (
+	ErrLokiQueryTooLong = errutil.BadRequest("loki.requestTooLong").MustTemplate(
+		"Request to Loki exceeded ({{.Public.QuerySize}} bytes) configured maximum size of {{.Public.MaxLimit}} bytes",
+		errutil.WithPublic("Query for Loki exceeded the configured limit of {{.Public.MaxLimit}} bytes. Remove some filters and try again."),
+	)
+)
+
+func NewErrLokiQueryTooLong(query string, maxLimit int) error {
+	return ErrLokiQueryTooLong.Build(errutil.TemplateData{
+		Private: map[string]any{
+			"query": query,
+		},
+		Public: map[string]any{
+			"MaxLimit":  maxLimit,
+			"QuerySize": len(query),
+		},
+	})
+}
+
 type remoteLokiClient interface {
 	Ping(context.Context) error
 	Push(context.Context, []Stream) error
 	RangeQuery(ctx context.Context, logQL string, start, end, limit int64) (QueryRes, error)
+	MaxQuerySize() int
 }
 
 // RemoteLokibackend is a state.Historian that records state history to an external Loki instance.
@@ -112,7 +133,7 @@ func (h *RemoteLokiBackend) Record(ctx context.Context, rule history_model.RuleM
 
 // Query retrieves state history entries from an external Loki instance and formats the results into a dataframe.
 func (h *RemoteLokiBackend) Query(ctx context.Context, query models.HistoryQuery) (*data.Frame, error) {
-	logQL, err := BuildLogQuery(query)
+	logQL, err := BuildLogQuery(query, h.client.MaxQuerySize())
 	if err != nil {
 		return nil, err
 	}
@@ -366,7 +387,9 @@ func isValidOperator(op string) bool {
 	return false
 }
 
-func BuildLogQuery(query models.HistoryQuery) (string, error) {
+// BuildLogQuery converts models.HistoryQuery and a list of folder UIDs to a Loki query.
+// Returns a Loki query or error if log query cannot be constructed. If user-defined query exceeds maximum allowed size returns ErrLokiQueryTooLong
+func BuildLogQuery(query models.HistoryQuery, maxQuerySize int) (string, error) {
 	selectors, err := buildSelectors(query)
 	if err != nil {
 		return "", fmt.Errorf("failed to build the provided selectors: %w", err)
@@ -400,6 +423,10 @@ func BuildLogQuery(query models.HistoryQuery) (string, error) {
 	}
 	logQL += labelFilters
 
+	if len(logQL) > maxQuerySize {
+		// if the query is too long even without filter by folders, then fail
+		return "", NewErrLokiQueryTooLong(logQL, maxQuerySize)
+	}
 	return logQL, nil
 }
 
diff --git a/pkg/services/ngalert/state/historian/loki_http.go b/pkg/services/ngalert/state/historian/loki_http.go
index 2d9ca11ba13..3e8b94a1585 100644
--- a/pkg/services/ngalert/state/historian/loki_http.go
+++ b/pkg/services/ngalert/state/historian/loki_http.go
@@ -42,6 +42,7 @@ type LokiConfig struct {
 	ExternalLabels    map[string]string
 	Encoder           encoder
 	MaxQueryLength    time.Duration
+	MaxQuerySize      int
 }
 
 func NewLokiConfig(cfg setting.UnifiedAlertingStateHistorySettings) (LokiConfig, error) {
@@ -77,6 +78,7 @@ func NewLokiConfig(cfg setting.UnifiedAlertingStateHistorySettings) (LokiConfig,
 		TenantID:          cfg.LokiTenantID,
 		ExternalLabels:    cfg.ExternalLabels,
 		MaxQueryLength:    cfg.LokiMaxQueryLength,
+		MaxQuerySize:      cfg.LokiMaxQuerySize,
 		// Snappy-compressed protobuf is the default, same goes for Promtail.
 		Encoder: SnappyProtoEncoder{},
 	}, nil
@@ -281,6 +283,10 @@ func (c *HttpLokiClient) RangeQuery(ctx context.Context, logQL string, start, en
 	return result, nil
 }
 
+func (c *HttpLokiClient) MaxQuerySize() int {
+	return c.cfg.MaxQuerySize
+}
+
 type QueryRes struct {
 	Data QueryData `json:"data"`
 }
diff --git a/pkg/services/ngalert/state/historian/loki_test.go b/pkg/services/ngalert/state/historian/loki_test.go
index dad1e0503a0..ac92673f06a 100644
--- a/pkg/services/ngalert/state/historian/loki_test.go
+++ b/pkg/services/ngalert/state/historian/loki_test.go
@@ -8,10 +8,15 @@ import (
 	"io"
 	"net/http"
 	"net/url"
+	"strings"
 	"testing"
 	"time"
 
 	"github.com/grafana/grafana-plugin-sdk-go/data"
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/testutil"
+	"github.com/stretchr/testify/require"
+
 	"github.com/grafana/grafana/pkg/infra/log"
 	"github.com/grafana/grafana/pkg/infra/tracing"
 	"github.com/grafana/grafana/pkg/services/ngalert/client"
@@ -20,9 +25,6 @@ import (
 	"github.com/grafana/grafana/pkg/services/ngalert/models"
 	"github.com/grafana/grafana/pkg/services/ngalert/state"
 	history_model "github.com/grafana/grafana/pkg/services/ngalert/state/historian/model"
-	"github.com/prometheus/client_golang/prometheus"
-	"github.com/prometheus/client_golang/prometheus/testutil"
-	"github.com/stretchr/testify/require"
 )
 
 func TestRemoteLokiBackend(t *testing.T) {
@@ -214,81 +216,110 @@ func TestRemoteLokiBackend(t *testing.T) {
 		selector, err = NewSelector("label", "invalid", "value")
 		require.Error(t, err)
 	})
+}
 
-	t.Run("buildLogQuery", func(t *testing.T) {
-		cases := []struct {
-			name  string
-			query models.HistoryQuery
-			exp   string
-		}{
-			{
-				name:  "default includes state history label and orgID label",
-				query: models.HistoryQuery{},
-				exp:   `{orgID="0",from="state-history"}`,
+func TestBuildLogQuery(t *testing.T) {
+	maxQuerySize := 110
+	cases := []struct {
+		name   string
+		query  models.HistoryQuery
+		exp    string
+		expErr error
+	}{
+		{
+			name:  "default includes state history label and orgID label",
+			query: models.HistoryQuery{},
+			exp:   `{orgID="0",from="state-history"}`,
+		},
+		{
+			name: "adds stream label filter for orgID",
+			query: models.HistoryQuery{
+				OrgID: 123,
 			},
-			{
-				name: "adds stream label filter for orgID",
-				query: models.HistoryQuery{
-					OrgID: 123,
+			exp: `{orgID="123",from="state-history"}`,
+		},
+		{
+			name: "filters ruleUID in log line",
+			query: models.HistoryQuery{
+				OrgID:   123,
+				RuleUID: "rule-uid",
+			},
+			exp: `{orgID="123",from="state-history"} | json | ruleUID="rule-uid"`,
+		},
+		{
+			name: "filters dashboardUID in log line",
+			query: models.HistoryQuery{
+				OrgID:        123,
+				DashboardUID: "dash-uid",
+			},
+			exp: `{orgID="123",from="state-history"} | json | dashboardUID="dash-uid"`,
+		},
+		{
+			name: "filters panelID in log line",
+			query: models.HistoryQuery{
+				OrgID:   123,
+				PanelID: 456,
+			},
+			exp: `{orgID="123",from="state-history"} | json | panelID=456`,
+		},
+		{
+			name: "filters instance labels in log line",
+			query: models.HistoryQuery{
+				OrgID: 123,
+				Labels: map[string]string{
+					"customlabel": "customvalue",
+					"labeltwo":    "labelvaluetwo",
 				},
-				exp: `{orgID="123",from="state-history"}`,
 			},
-			{
-				name: "filters ruleUID in log line",
-				query: models.HistoryQuery{
-					OrgID:   123,
-					RuleUID: "rule-uid",
+			exp: `{orgID="123",from="state-history"} | json | labels_customlabel="customvalue" | labels_labeltwo="labelvaluetwo"`,
+		},
+		{
+			name: "filters both instance labels + ruleUID",
+			query: models.HistoryQuery{
+				OrgID:   123,
+				RuleUID: "rule-uid",
+				Labels: map[string]string{
+					"customlabel": "customvalue",
 				},
-				exp: `{orgID="123",from="state-history"} | json | ruleUID="rule-uid"`,
 			},
-			{
-				name: "filters dashboardUID in log line",
-				query: models.HistoryQuery{
-					OrgID:        123,
-					DashboardUID: "dash-uid",
+			exp: `{orgID="123",from="state-history"} | json | ruleUID="rule-uid" | labels_customlabel="customvalue"`,
+		},
+		{
+			name: "should return if query does not exceed max limit",
+			query: models.HistoryQuery{
+				OrgID:   123,
+				RuleUID: "rule-uid",
+				Labels: map[string]string{
+					"customlabel": strings.Repeat("!", 24),
 				},
-				exp: `{orgID="123",from="state-history"} | json | dashboardUID="dash-uid"`,
 			},
-			{
-				name: "filters panelID in log line",
-				query: models.HistoryQuery{
-					OrgID:   123,
-					PanelID: 456,
+			exp: `{orgID="123",from="state-history"} | json | ruleUID="rule-uid" | labels_customlabel="!!!!!!!!!!!!!!!!!!!!!!!!"`,
+		},
+		{
+			name: "should return error if query is too long",
+			query: models.HistoryQuery{
+				OrgID:   123,
+				RuleUID: "rule-uid",
+				Labels: map[string]string{
+					"customlabel": strings.Repeat("!", 25),
 				},
-				exp: `{orgID="123",from="state-history"} | json | panelID=456`,
 			},
-			{
-				name: "filters instance labels in log line",
-				query: models.HistoryQuery{
-					OrgID: 123,
-					Labels: map[string]string{
-						"customlabel": "customvalue",
-						"labeltwo":    "labelvaluetwo",
-					},
-				},
-				exp: `{orgID="123",from="state-history"} | json | labels_customlabel="customvalue" | labels_labeltwo="labelvaluetwo"`,
-			},
-			{
-				name: "filters both instance labels + ruleUID",
-				query: models.HistoryQuery{
-					OrgID:   123,
-					RuleUID: "rule-uid",
-					Labels: map[string]string{
-						"customlabel": "customvalue",
-					},
-				},
-				exp: `{orgID="123",from="state-history"} | json | ruleUID="rule-uid" | labels_customlabel="customvalue"`,
-			},
-		}
+			expErr: ErrLokiQueryTooLong,
+		},
+	}
 
-		for _, tc := range cases {
-			t.Run(tc.name, func(t *testing.T) {
-				res, err := BuildLogQuery(tc.query)
-				require.NoError(t, err)
-				require.Equal(t, tc.exp, res)
-			})
-		}
-	})
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			res, err := BuildLogQuery(tc.query, maxQuerySize)
+			if tc.expErr != nil {
+				require.ErrorIs(t, err, tc.expErr)
+				return
+			}
+			require.LessOrEqual(t, len(res), maxQuerySize)
+			require.NoError(t, err)
+			require.Equal(t, tc.exp, res)
+		})
+	}
 }
 
 func TestMerge(t *testing.T) {
diff --git a/pkg/setting/setting_unified_alerting.go b/pkg/setting/setting_unified_alerting.go
index 1d205dc6faa..0f6a199bf5f 100644
--- a/pkg/setting/setting_unified_alerting.go
+++ b/pkg/setting/setting_unified_alerting.go
@@ -64,6 +64,7 @@ const (
 	stateHistoryDefaultEnabled     = true
 	lokiDefaultMaxQueryLength      = 721 * time.Hour // 30d1h, matches the default value in Loki
 	defaultRecordingRequestTimeout = 10 * time.Second
+	lokiDefaultMaxQuerySize        = 65536 // 64kb
 )
 
 type UnifiedAlertingSettings struct {
@@ -160,6 +161,7 @@ type UnifiedAlertingStateHistorySettings struct {
 	LokiBasicAuthPassword string
 	LokiBasicAuthUsername string
 	LokiMaxQueryLength    time.Duration
+	LokiMaxQuerySize      int
 	MultiPrimary          string
 	MultiSecondaries      []string
 	ExternalLabels        map[string]string
@@ -404,6 +406,7 @@ func (cfg *Cfg) ReadUnifiedAlertingSettings(iniFile *ini.File) error {
 		LokiBasicAuthUsername: stateHistory.Key("loki_basic_auth_username").MustString(""),
 		LokiBasicAuthPassword: stateHistory.Key("loki_basic_auth_password").MustString(""),
 		LokiMaxQueryLength:    stateHistory.Key("loki_max_query_length").MustDuration(lokiDefaultMaxQueryLength),
+		LokiMaxQuerySize:      stateHistory.Key("loki_max_query_size").MustInt(lokiDefaultMaxQuerySize),
 		MultiPrimary:          stateHistory.Key("primary").MustString(""),
 		MultiSecondaries:      splitTrim(stateHistory.Key("secondaries").MustString(""), ","),
 		ExternalLabels:        stateHistoryLabels.KeysHash(),