diff --git a/api/go.mod b/api/go.mod
index 38ee77308..d7e944945 100644
--- a/api/go.mod
+++ b/api/go.mod
@@ -52,7 +52,7 @@ require (
 	golang.org/x/exp v0.0.0-20230321023759-10a507213a29
 	golang.org/x/mod v0.9.0
 	golang.org/x/oauth2 v0.6.0
-	golang.org/x/sync v0.1.0
+	golang.org/x/sync v0.5.0
 	gopkg.in/alecthomas/kingpin.v2 v2.2.6
 	gopkg.in/yaml.v3 v3.0.1
 	k8s.io/api v0.27.4
diff --git a/api/go.sum b/api/go.sum
index fd9bb6d7e..98380d1fc 100644
--- a/api/go.sum
+++ b/api/go.sum
@@ -318,10 +318,6 @@ github.com/portainer/libhttp v0.0.0-20230615144939-a999f666d9a9 h1:Jq8g/pDcFL1Z/
 github.com/portainer/libhttp v0.0.0-20230615144939-a999f666d9a9/go.mod h1:H49JLiywwLt2rrJVroafEWy8fIs0i7mThAThK40sbb8=
 github.com/portainer/portainer/pkg/featureflags v0.0.0-20230711022654-64b227b2e146 h1:8JVXjyFhGgSogKGOddnOROZxBEeWNvvo3EPT9uIJ2Xo=
 github.com/portainer/portainer/pkg/featureflags v0.0.0-20230711022654-64b227b2e146/go.mod h1:x4Lpq/BjFhZmuNB8e8FO0ObRPQ/Z/V9rTe54bMedf1A=
-github.com/portainer/portainer/pkg/libhelm v0.0.0-20230711022654-64b227b2e146 h1:1qW7quKyFG4tOnMcnnqyYsDVfL09etO1h/Cu/3ak7KU=
-github.com/portainer/portainer/pkg/libhelm v0.0.0-20230711022654-64b227b2e146/go.mod h1:cFRD6PvOwpd2pf/O1r/IMKl+ZB12pWfo/Evleh3aCfM=
-github.com/portainer/portainer/pkg/libhelm v0.0.0-20230919060741-8f42ba025479 h1:DbmhSQZpDo5f0cr+CKLJqoqhQiuxp8QFXdZsjPS1lI4=
-github.com/portainer/portainer/pkg/libhelm v0.0.0-20230919060741-8f42ba025479/go.mod h1:cFRD6PvOwpd2pf/O1r/IMKl+ZB12pWfo/Evleh3aCfM=
 github.com/portainer/portainer/pkg/libhelm v0.0.0-20230928223730-157393c965ce h1:DQTMXYH1zn2DzuAe+4rT40JqdHLhpHHJ2pzRFhvZ/+c=
 github.com/portainer/portainer/pkg/libhelm v0.0.0-20230928223730-157393c965ce/go.mod h1:cFRD6PvOwpd2pf/O1r/IMKl+ZB12pWfo/Evleh3aCfM=
 github.com/portainer/portainer/pkg/libstack v0.0.0-20230711022654-64b227b2e146 h1:ZGj+j5HoajaO+mXgCm6NzOU+zUdIlJK2amagB+QIDvc=
@@ -442,6 +438,8 @@ golang.org/x/sync v0.0.0-20201020160332-67f06af15bc9/go.mod h1:RxMgew5VJxzue5/jJ
 golang.org/x/sync v0.0.0-20210220032951-036812b2e83c/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.1.0 h1:wsuoTGHzEhffawBOhz5CYhcrV4IdKZbEyZjBMuTp12o=
 golang.org/x/sync v0.1.0/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
+golang.org/x/sync v0.5.0 h1:60k92dhOjHxJkrqnwsfl8KuaHbn/5dl0lUPUklKo3qE=
+golang.org/x/sync v0.5.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
 golang.org/x/sys v0.0.0-20180830151530-49385e6e1522/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20180905080454-ebe1bf3edb33/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20190215142949-d0b11bdaac8a/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
diff --git a/api/stacks/deployments/deploy.go b/api/stacks/deployments/deploy.go
index b5111de02..89e5977a8 100644
--- a/api/stacks/deployments/deploy.go
+++ b/api/stacks/deployments/deploy.go
@@ -3,6 +3,7 @@ package deployments
 import (
 	"crypto/tls"
 	"fmt"
+	"strconv"
 	"time"
 
 	portainer "github.com/portainer/portainer/api"
@@ -16,6 +17,7 @@ import (
 
 	"github.com/pkg/errors"
 	"github.com/rs/zerolog/log"
+	"golang.org/x/sync/singleflight"
 )
 
 type StackAuthorMissingErr struct {
@@ -27,9 +29,19 @@ func (e *StackAuthorMissingErr) Error() string {
 	return fmt.Sprintf("stack's %v author %s is missing", e.stackID, e.authorName)
 }
 
+var singleflightGroup = &singleflight.Group{}
+
 // RedeployWhenChanged pull and redeploy the stack when git repo changed
 // Stack will always be redeployed if force deployment is set to true
 func RedeployWhenChanged(stackID portainer.StackID, deployer StackDeployer, datastore dataservices.DataStore, gitService portainer.GitService) error {
+	_, err, _ := singleflightGroup.Do(strconv.Itoa(int(stackID)), func() (any, error) {
+		return nil, redeployWhenChanged(stackID, deployer, datastore, gitService)
+	})
+
+	return err
+}
+
+func redeployWhenChanged(stackID portainer.StackID, deployer StackDeployer, datastore dataservices.DataStore, gitService portainer.GitService) error {
 	log.Debug().Int("stack_id", int(stackID)).Msg("redeploying stack")
 
 	stack, err := datastore.Stack().Read(stackID)
diff --git a/go.work b/go.work
index df63092d4..163ede790 100644
--- a/go.work
+++ b/go.work
@@ -1,4 +1,6 @@
-go 1.19
+go 1.20
+
+toolchain go1.21.0
 
 use (
 	./api