diff --git a/api/http/handler/endpoints/endpoint_association_delete.go b/api/http/handler/endpoints/endpoint_association_delete.go
index ad294c883..c7f9046c8 100644
--- a/api/http/handler/endpoints/endpoint_association_delete.go
+++ b/api/http/handler/endpoints/endpoint_association_delete.go
@@ -1,14 +1,17 @@
 package endpoints
 
 import (
+	"encoding/base64"
 	"errors"
-	"net/http"
-
+	"fmt"
 	httperror "github.com/portainer/libhttp/error"
 	"github.com/portainer/libhttp/request"
 	"github.com/portainer/libhttp/response"
 	portainer "github.com/portainer/portainer/api"
 	bolterrors "github.com/portainer/portainer/api/bolt/errors"
+	"net/http"
+	"regexp"
+	"strings"
 )
 
 // @id EndpointAssociationDelete
@@ -45,6 +48,11 @@ func (handler *Handler) endpointAssociationDelete(w http.ResponseWriter, r *http
 	endpoint.Snapshots = []portainer.DockerSnapshot{}
 	endpoint.Kubernetes.Snapshots = []portainer.KubernetesSnapshot{}
 
+	endpoint.EdgeKey, err = handler.updateEdgeKey(endpoint.EdgeKey)
+	if err != nil {
+		return &httperror.HandlerError{http.StatusInternalServerError, "Invalid EdgeKey", err}
+	}
+
 	err = handler.DataStore.Endpoint().UpdateEndpoint(portainer.EndpointID(endpointID), endpoint)
 	if err != nil {
 		return &httperror.HandlerError{http.StatusInternalServerError, "Failed persisting endpoint in database", err}
@@ -54,3 +62,27 @@ func (handler *Handler) endpointAssociationDelete(w http.ResponseWriter, r *http
 
 	return response.JSON(w, endpoint)
 }
+
+func (handler *Handler) updateEdgeKey(edgeKey string) (string, error) {
+	oldEdgeKeyByte, err := base64.RawStdEncoding.DecodeString(edgeKey)
+	if err != nil {
+		return "", err
+	}
+
+	oldEdgeKeyStr := string(oldEdgeKeyByte)
+
+	httpPort := getPort(handler.BindAddress)
+	httpsPort := getPort(handler.BindAddressHTTPS)
+
+	// replace "http://" with "https://" and replace ":9000" with ":9443", in the case of default values
+	// oldEdgeKeyStr example: http://10.116.1.178:9000|10.116.1.178:8000|46:99:4a:8d:a6:de:6a:bd:d8:e2:1c:99:81:60:54:55|52
+	r := regexp.MustCompile(fmt.Sprintf("^(http://)([^|]+)(:%s)(|.*)", httpPort))
+	newEdgeKeyStr := r.ReplaceAllString(oldEdgeKeyStr, fmt.Sprintf("https://$2:%s$4", httpsPort))
+
+	return base64.RawStdEncoding.EncodeToString([]byte(newEdgeKeyStr)), nil
+}
+
+func getPort(url string) string {
+	items := strings.Split(url, ":")
+	return items[len(items) - 1]
+}
diff --git a/api/http/handler/endpoints/handler.go b/api/http/handler/endpoints/handler.go
index 25f8d18a0..592134d1f 100644
--- a/api/http/handler/endpoints/handler.go
+++ b/api/http/handler/endpoints/handler.go
@@ -32,6 +32,8 @@ type Handler struct {
 	K8sClientFactory     *cli.ClientFactory
 	ComposeStackManager  portainer.ComposeStackManager
 	AuthorizationService *authorization.Service
+	BindAddress          string
+	BindAddressHTTPS     string
 }
 
 // NewHandler creates a handler to manage endpoint operations.
diff --git a/api/http/server.go b/api/http/server.go
index a38c1922a..951a7e4ae 100644
--- a/api/http/server.go
+++ b/api/http/server.go
@@ -143,6 +143,8 @@ func (server *Server) Start() error {
 	endpointHandler.ReverseTunnelService = server.ReverseTunnelService
 	endpointHandler.ComposeStackManager = server.ComposeStackManager
 	endpointHandler.AuthorizationService = server.AuthorizationService
+	endpointHandler.BindAddress = server.BindAddress
+	endpointHandler.BindAddressHTTPS = server.BindAddressHTTPS
 
 	var endpointEdgeHandler = endpointedge.NewHandler(requestBouncer)
 	endpointEdgeHandler.DataStore = server.DataStore