diff --git a/api/docker/container.go b/api/docker/container.go
index c1e0631b4..2d5c1e426 100644
--- a/api/docker/container.go
+++ b/api/docker/container.go
@@ -9,6 +9,7 @@ import (
 	dockerclient "github.com/portainer/portainer/api/docker/client"
 	"github.com/portainer/portainer/api/docker/images"
 
+	"github.com/Masterminds/semver"
 	"github.com/docker/docker/api/types"
 	dockercontainer "github.com/docker/docker/api/types/container"
 	"github.com/docker/docker/api/types/network"
@@ -30,6 +31,44 @@ func NewContainerService(factory *dockerclient.ClientFactory, dataStore dataserv
 	}
 }
 
+// applyVersionConstraint uses the version to apply a transformation function to
+// the value when the constraint is satisfied
+func applyVersionConstraint[T any](currentVersion, versionConstraint string, value T, transform func(T) T) (T, error) {
+	newValue := value
+
+	constraint, err := semver.NewConstraint(versionConstraint)
+	if err != nil {
+		return newValue, errors.New("invalid version constraint specified")
+	}
+
+	currentVer, err := semver.NewVersion(currentVersion)
+	if err != nil {
+		log.Warn().Err(err).Msg("Unable to parse the Docker client version")
+
+		return newValue, nil
+	}
+
+	if satisfiesConstraint, _ := constraint.Validate(currentVer); satisfiesConstraint {
+		newValue = transform(value)
+	}
+
+	return newValue, nil
+}
+
+func clearMacAddrs(n network.NetworkingConfig) network.NetworkingConfig {
+	netConfig := network.NetworkingConfig{
+		EndpointsConfig: make(map[string]*network.EndpointSettings),
+	}
+
+	for k := range n.EndpointsConfig {
+		endpointConfig := n.EndpointsConfig[k].Copy()
+		endpointConfig.MacAddress = ""
+		netConfig.EndpointsConfig[k] = endpointConfig
+	}
+
+	return netConfig
+}
+
 // Recreate a container
 func (c *ContainerService) Recreate(ctx context.Context, endpoint *portainer.Endpoint, containerId string, forcePullImage bool, imageTag, nodeName string) (*types.ContainerJSON, error) {
 	cli, err := c.factory.CreateClient(endpoint, nodeName, nil)
@@ -83,7 +122,7 @@ func (c *ContainerService) Recreate(ctx context.Context, endpoint *portainer.End
 		return nil, errors.Wrap(err, "rename container error")
 	}
 
-	networkWithCreation := network.NetworkingConfig{
+	initialNetwork := network.NetworkingConfig{
 		EndpointsConfig: make(map[string]*network.EndpointSettings),
 	}
 
@@ -95,10 +134,10 @@ func (c *ContainerService) Recreate(ctx context.Context, endpoint *portainer.End
 		}
 
 		// 5. get the first network attached to the current container
-		if len(networkWithCreation.EndpointsConfig) == 0 {
+		if len(initialNetwork.EndpointsConfig) == 0 {
 			// Retrieve the first network that is linked to the present container, which
 			// will be utilized when creating the container.
-			networkWithCreation.EndpointsConfig[name] = network
+			initialNetwork.EndpointsConfig[name] = network
 		}
 	}
 	c.sr.enable()
@@ -124,7 +163,15 @@ func (c *ContainerService) Recreate(ctx context.Context, endpoint *portainer.End
 	// to retain the same network settings we have to connect on creation to one of the old
 	// container's networks, and connect to the other networks after creation.
 	// see: https://portainer.atlassian.net/browse/EE-5448
-	create, err := cli.ContainerCreate(ctx, container.Config, container.HostConfig, &networkWithCreation, nil, container.Name)
+
+	// Docker API < 1.44 does not support specifying MAC addresses
+	// https://github.com/moby/moby/blob/6aea26b431ea152a8b085e453da06ea403f89886/client/container_create.go#L44-L46
+	initialNetwork, err = applyVersionConstraint(cli.ClientVersion(), "< 1.44", initialNetwork, clearMacAddrs)
+	if err != nil {
+		return nil, err
+	}
+
+	create, err := cli.ContainerCreate(ctx, container.Config, container.HostConfig, &initialNetwork, nil, container.Name)
 
 	c.sr.push(func() {
 		log.Debug().Str("container_id", create.ID).Msg("removing the new container")
@@ -144,7 +191,7 @@ func (c *ContainerService) Recreate(ctx context.Context, endpoint *portainer.End
 	log.Debug().Str("container_id", newContainerId).Msg("connecting networks to container")
 	networks := container.NetworkSettings.Networks
 	for key, network := range networks {
-		if _, ok := networkWithCreation.EndpointsConfig[key]; ok {
+		if _, ok := initialNetwork.EndpointsConfig[key]; ok {
 			// skip the network that is used during container creation
 			continue
 		}
diff --git a/api/docker/container_test.go b/api/docker/container_test.go
new file mode 100644
index 000000000..e3d9e0bd8
--- /dev/null
+++ b/api/docker/container_test.go
@@ -0,0 +1,52 @@
+package docker
+
+import (
+	"testing"
+
+	"github.com/docker/docker/api/types/network"
+	"github.com/stretchr/testify/require"
+)
+
+func TestApplyVersionConstraint(t *testing.T) {
+	initialNet := network.NetworkingConfig{
+		EndpointsConfig: map[string]*network.EndpointSettings{
+			"key1": {
+				MacAddress: "mac1",
+				EndpointID: "endpointID1",
+			},
+			"key2": {
+				MacAddress: "mac2",
+				EndpointID: "endpointID2",
+			},
+		},
+	}
+
+	f := func(currentVer string, constraint string, success, emptyMac bool) {
+		t.Helper()
+
+		transformedNet, err := applyVersionConstraint(currentVer, constraint, initialNet, clearMacAddrs)
+		if success {
+			require.NoError(t, err)
+		} else {
+			require.Error(t, err)
+		}
+
+		require.Len(t, transformedNet.EndpointsConfig, len(initialNet.EndpointsConfig))
+
+		for k := range initialNet.EndpointsConfig {
+			if emptyMac {
+				require.NotEqual(t, initialNet.EndpointsConfig[k], transformedNet.EndpointsConfig[k])
+				require.Empty(t, transformedNet.EndpointsConfig[k].MacAddress)
+
+				continue
+			}
+
+			require.Equal(t, initialNet.EndpointsConfig[k], transformedNet.EndpointsConfig[k])
+		}
+	}
+
+	f("1.45", "< 1.44", true, false)  // No transformation
+	f("1.43", "< 1.44", true, true)   // Transformation
+	f("a.b.", "< 1.44", true, false)  // Invalid current version
+	f("1.45", "z 1.44", false, false) // Invalid version constraint
+}