diff --git a/update/application.go b/update/application.go
index ba4ffc22..875f87fc 100644
--- a/update/application.go
+++ b/update/application.go
@@ -17,6 +17,9 @@ import (
 	"k8s.io/utils/ptr"
 )
 
+// ReleaseTrigger is used to request a new release for the application.
+const ReleaseTrigger = "RELEASE_TRIGGER"
+
 // BuildTrigger is used to request a retry-build for the application.
 const BuildTrigger = "BUILD_TRIGGER"
 
@@ -40,7 +43,8 @@ type applicationCmd struct {
 	ScheduledJob             *scheduledJob     `embed:"" prefix:"scheduled-job-"`
 	DeleteWorkerJob          *string           `help:"Delete a worker job by name"`
 	DeleteScheduledJob       *string           `help:"Delete a scheduled job by name"`
-	RetryBuild               *bool             `help:"Retries build for the application if set to true." placeholder:"false"`
+	RetryRelease             *bool             `help:"Retries release for the application." placeholder:"false"`
+	RetryBuild               *bool             `help:"Retries build for the application." placeholder:"false"`
 	GitInformationServiceURL string            `help:"URL of the git information service." default:"https://git-info.deplo.io" env:"GIT_INFORMATION_SERVICE_URL" hidden:""`
 	SkipRepoAccessCheck      bool              `help:"Skip the git repository access check" default:"false"`
 	Debug                    bool              `help:"Enable debug messages" default:"false"`
@@ -244,21 +248,26 @@ func (cmd *applicationCmd) applyUpdates(app *apps.Application) {
 		app.Spec.ForProvider.Language = apps.Language(*cmd.Language)
 	}
 
+	runtimeEnv := make(map[string]string)
+	if cmd.Env != nil {
+		runtimeEnv = cmd.Env
+	}
+	if cmd.RetryRelease != nil && *cmd.RetryRelease {
+		runtimeEnv[ReleaseTrigger] = triggerTimestamp()
+	}
 	var delEnv []string
 	if cmd.DeleteEnv != nil {
 		delEnv = *cmd.DeleteEnv
 	}
-	app.Spec.ForProvider.Config.Env = util.UpdateEnvVars(app.Spec.ForProvider.Config.Env, cmd.Env, delEnv)
+	app.Spec.ForProvider.Config.Env = util.UpdateEnvVars(app.Spec.ForProvider.Config.Env, runtimeEnv, delEnv)
 
 	buildEnv := make(map[string]string)
 	if cmd.BuildEnv != nil {
 		buildEnv = cmd.BuildEnv
 	}
-
 	if cmd.RetryBuild != nil && *cmd.RetryBuild {
-		buildEnv[BuildTrigger] = time.Now().UTC().Format(time.RFC3339)
+		buildEnv[BuildTrigger] = triggerTimestamp()
 	}
-
 	var buildDelEnv []string
 	if cmd.DeleteBuildEnv != nil {
 		buildDelEnv = *cmd.DeleteBuildEnv
@@ -276,6 +285,10 @@ func (cmd *applicationCmd) applyUpdates(app *apps.Application) {
 	}
 }
 
+func triggerTimestamp() string {
+	return time.Now().UTC().Format(time.RFC3339)
+}
+
 func (job deployJob) applyUpdates(cfg *apps.Config) {
 	if job.Enabled != nil && !*job.Enabled {
 		// if enabled is explicitly set to false we set the DeployJob field to
diff --git a/update/application_test.go b/update/application_test.go
index 61f23628..ac8e04c4 100644
--- a/update/application_test.go
+++ b/update/application_test.go
@@ -142,7 +142,8 @@ func TestApplication(t *testing.T) {
 				assert.Equal(t, *cmd.DeployJob.Name, updated.Spec.ForProvider.Config.DeployJob.Name)
 				assert.Equal(t, *cmd.DeployJob.Timeout, updated.Spec.ForProvider.Config.DeployJob.Timeout.Duration)
 				assert.Equal(t, *cmd.DeployJob.Retries, *updated.Spec.ForProvider.Config.DeployJob.Retries)
-				// RetryBuild should be not set by default:
+				// Retry Release/Build should be not set by default:
+				assert.Nil(t, util.EnvVarByName(updated.Spec.ForProvider.Config.Env, ReleaseTrigger))
 				assert.Nil(t, util.EnvVarByName(updated.Spec.ForProvider.BuildEnv, BuildTrigger))
 			},
 		},
@@ -359,6 +360,30 @@ func TestApplication(t *testing.T) {
 				assert.Nil(t, updated.Spec.ForProvider.Config.DeployJob)
 			},
 		},
+		"retry release": {
+			orig: existingApp,
+			cmd: applicationCmd{
+				resourceCmd: resourceCmd{
+					Name: existingApp.Name,
+				},
+				RetryRelease: ptr.To(true),
+			},
+			checkApp: func(t *testing.T, cmd applicationCmd, orig, updated *apps.Application) {
+				assert.NotNil(t, util.EnvVarByName(updated.Spec.ForProvider.Config.Env, ReleaseTrigger))
+			},
+		},
+		"do not retry release": {
+			orig: existingApp,
+			cmd: applicationCmd{
+				resourceCmd: resourceCmd{
+					Name: existingApp.Name,
+				},
+				RetryRelease: ptr.To(false),
+			},
+			checkApp: func(t *testing.T, cmd applicationCmd, orig, updated *apps.Application) {
+				assert.Nil(t, util.EnvVarByName(updated.Spec.ForProvider.Config.Env, ReleaseTrigger))
+			},
+		},
 		"retry build": {
 			orig: existingApp,
 			cmd: applicationCmd{