diff --git a/components/ide/jetbrains/backend-plugin/launch-dev-server.sh b/components/ide/jetbrains/backend-plugin/launch-dev-server.sh
index 6e02a8996bae32..7c658fb4ac8717 100755
--- a/components/ide/jetbrains/backend-plugin/launch-dev-server.sh
+++ b/components/ide/jetbrains/backend-plugin/launch-dev-server.sh
@@ -39,4 +39,14 @@ export IJ_HOST_SYSTEM_BASE_DIR=/workspace/.cache/JetBrains
 # Enable host status endpoint
 export CWM_HOST_STATUS_OVER_HTTP_TOKEN=gitpod
 
-$TEST_BACKEND_DIR/bin/remote-dev-server.sh run $TEST_DIR
\ No newline at end of file
+# Build and move idea-cli, then overwrite environment variables initially defined by `components/ide/jetbrains/image/leeway.Dockerfile`
+IDEA_CLI_DEV_PATH=/ide-desktop/bin/idea-cli-dev
+(cd ../cli && go build -o $IDEA_CLI_DEV_PATH)
+export EDITOR="$IDEA_CLI_DEV_PATH open"
+export VISUAL="$EDITOR"
+export GP_OPEN_EDITOR="$EDITOR"
+export GIT_EDITOR="$EDITOR --wait"
+export GP_PREVIEW_BROWSER="$IDEA_CLI_DEV_PATH preview"
+export GP_EXTERNAL_BROWSER="$IDEA_CLI_DEV_PATH preview"
+
+$TEST_BACKEND_DIR/bin/remote-dev-server.sh run $TEST_DIR
diff --git a/components/ide/jetbrains/backend-plugin/src/main/kotlin/io/gitpod/jetbrains/remote/GitpodCLIService.kt b/components/ide/jetbrains/backend-plugin/src/main/kotlin/io/gitpod/jetbrains/remote/GitpodCLIService.kt
index a8fd8be4145cf6..77c36c0d5958f0 100644
--- a/components/ide/jetbrains/backend-plugin/src/main/kotlin/io/gitpod/jetbrains/remote/GitpodCLIService.kt
+++ b/components/ide/jetbrains/backend-plugin/src/main/kotlin/io/gitpod/jetbrains/remote/GitpodCLIService.kt
@@ -7,6 +7,7 @@ package io.gitpod.jetbrains.remote
 import com.intellij.codeWithMe.ClientId
 import com.intellij.ide.BrowserUtil
 import com.intellij.ide.CommandLineProcessor
+import com.intellij.openapi.application.ApplicationManager
 import com.intellij.openapi.client.ClientSession
 import com.intellij.openapi.client.ClientSessionsManager
 import com.intellij.openapi.diagnostic.thisLogger
@@ -20,7 +21,7 @@ import org.jetbrains.ide.RestService
 import java.nio.file.InvalidPathException
 import java.nio.file.Path
 
-
+@Suppress("UnstableApiUsage")
 class GitpodCLIService : RestService() {
 
     override fun getServiceName() = SERVICE_NAME
@@ -54,22 +55,37 @@ class GitpodCLIService : RestService() {
     }
 
     private fun withClient(request: FullHttpRequest, context: ChannelHandlerContext, action: (project: Project?) -> Unit): String? {
+        ApplicationManager.getApplication().executeOnPooledThread {
+            getClientSessionAndProjectAsync().let {
+                ClientId.withClientId(it.session.clientId) {
+                    action(it.project)
+                    sendOk(request, context)
+                }
+            }
+        }
+        return null
+    }
+
+    private data class ClientSessionAndProject(val session: ClientSession, val project: Project?)
+
+    private tailrec fun getClientSessionAndProjectAsync(): ClientSessionAndProject {
         val project = getLastFocusedOrOpenedProject()
         var session: ClientSession? = null
         if (project != null) {
-            session = ClientSessionsManager.getProjectSessions(project, false).first()
+            session = ClientSessionsManager.getProjectSessions(project, false).firstOrNull()
         }
         if (session == null) {
-            session = ClientSessionsManager.getAppSessions(false).first()
+            session = ClientSessionsManager.getAppSessions(false).firstOrNull()
         }
-        if (session == null) {
-            return "no client"
+        return if (session != null) {
+            ClientSessionAndProject (
+                 session = session,
+                 project = project
+            )
+        } else {
+            Thread.sleep(1000L)
+            getClientSessionAndProjectAsync()
         }
-        ClientId.withClientId(session.clientId) {
-            action(project)
-        }
-        sendOk(request, context)
-        return null
     }
 
     private fun parseFilePath(path: String): Path? {
@@ -88,4 +104,4 @@ class GitpodCLIService : RestService() {
     companion object {
         const val SERVICE_NAME = "gitpod/cli"
     }
-}
\ No newline at end of file
+}
diff --git a/components/ide/jetbrains/cli/cmd/open.go b/components/ide/jetbrains/cli/cmd/open.go
index 8d637f42574bc7..e49a72fbef3792 100644
--- a/components/ide/jetbrains/cli/cmd/open.go
+++ b/components/ide/jetbrains/cli/cmd/open.go
@@ -8,7 +8,6 @@ import (
 	"fmt"
 	"log"
 	"net/http"
-	"net/url"
 	"path/filepath"
 
 	"github.com/spf13/cobra"
@@ -25,10 +24,7 @@ var openCmd = &cobra.Command{
 			log.Fatal(err)
 		}
 
-		url, err := url.Parse("http://localhost:63342/api/gitpod/cli")
-		if err != nil {
-			log.Fatal(err)
-		}
+		url := getCliApiUrl()
 		query := url.Query()
 		query.Add("op", "open")
 		query.Add("file", file)
diff --git a/components/ide/jetbrains/cli/cmd/preview.go b/components/ide/jetbrains/cli/cmd/preview.go
index fc78be97fad3d3..77f89f47ebbbfc 100644
--- a/components/ide/jetbrains/cli/cmd/preview.go
+++ b/components/ide/jetbrains/cli/cmd/preview.go
@@ -7,7 +7,6 @@ package cmd
 import (
 	"log"
 	"net/http"
-	"net/url"
 
 	"github.com/spf13/cobra"
 )
@@ -15,10 +14,7 @@ import (
 var previewCmd = &cobra.Command{
 	Use: "preview",
 	Run: func(cmd *cobra.Command, args []string) {
-		url, err := url.Parse("http://localhost:63342/api/gitpod/cli")
-		if err != nil {
-			log.Fatal(err)
-		}
+		url := getCliApiUrl()
 		query := url.Query()
 		query.Add("op", "preview")
 		query.Add("url", args[0])
diff --git a/components/ide/jetbrains/cli/cmd/root.go b/components/ide/jetbrains/cli/cmd/root.go
index 9f44d048853be5..aa10341de094de 100644
--- a/components/ide/jetbrains/cli/cmd/root.go
+++ b/components/ide/jetbrains/cli/cmd/root.go
@@ -5,7 +5,11 @@
 package cmd
 
 import (
+	"errors"
+	"log"
+	"net/url"
 	"os"
+	"strconv"
 
 	"github.com/spf13/cobra"
 )
@@ -21,4 +25,16 @@ func Execute() {
 	}
 }
 
+func getCliApiUrl() *url.URL {
+	var backendPort = 63342
+	if _, fileStatError := os.Stat("/ide-desktop/bin/idea-cli-dev"); !errors.Is(fileStatError, os.ErrNotExist) {
+		backendPort = backendPort + 1
+	}
+	parsedUrl, urlParseError := url.Parse("http://localhost:" + strconv.Itoa(backendPort) + "/api/gitpod/cli")
+	if urlParseError != nil {
+		log.Fatal(urlParseError)
+	}
+	return parsedUrl
+}
+
 func init() {}