diff --git a/.vscode/launch.json b/.vscode/launch.json
index b74e0acda049..a35df3d79d7c 100644
--- a/.vscode/launch.json
+++ b/.vscode/launch.json
@@ -15,6 +15,14 @@
 			"preLaunchTask": "Build All",
 			"dmb": "${workspaceFolder}/${command:CurrentDMB}",
 			"dreamDaemon": true
+		},
+		{
+			"type": "byond",
+			"request": "launch",
+			"name": "Launch Both",
+			"preLaunchTask": "Build and Launch Server",
+			"dmb": "${workspaceFolder}/${command:CurrentDMB}",
+			"dreamDaemon": true
 		}
 	]
 }
diff --git a/.vscode/tasks.json b/.vscode/tasks.json
index b7d646518bdb..7edef5a57a87 100644
--- a/.vscode/tasks.json
+++ b/.vscode/tasks.json
@@ -100,6 +100,29 @@
 			},
 			"group": "build",
 			"label": "tgui: clean",
+		},
+		{
+		    "type": "shell",
+		    "label": "Background: Wait for DreamDaemon",
+		    "command": "start",
+		    "args": ["\"Waiting for DreamDaemon\"", "powershell", "-ExecutionPolicy", "Bypass", "-File", "${workspaceFolder}\\bin\\connect-to-local-wait.ps1"],
+		    "options": {
+		        "shell": {
+		            "executable": "cmd.exe", // it needs to detach so vscode can actually launch dreamdaemon before we start waiting for it
+		            "args": ["/c"]
+		        }
+		    },
+		    "presentation": {
+		        "reveal": "silent"
+		    },
+		    "problemMatcher": []
+		},
+		{
+			"type": "shell",
+			"label": "Build and Launch Server",
+			"dependsOn": ["Build All", "Background: Wait for DreamDaemon"],
+			"dependsOrder": "parallel",
+			"problemMatcher": []
 		}
 	]
 }
diff --git a/bin/connect-to-local-wait.ps1 b/bin/connect-to-local-wait.ps1
new file mode 100644
index 000000000000..4bfee1b09a0e
--- /dev/null
+++ b/bin/connect-to-local-wait.ps1
@@ -0,0 +1,83 @@
+# Ping the local DreamDaemon server until it responds
+# Autodetects port by finding what dreamdaemon.exe is listening on
+
+function Find-DreamDaemonPort {
+	# check running processes, this is slow as shit because it looks at everything so erroraction should be faster
+    $proc = Get-Process -Name 'dd','dreamdaemon' -ErrorAction SilentlyContinue | Select-Object -First 1
+    if (-not $proc) {
+        return $null
+    }
+
+	# found the process, get the port
+    $conn = Get-NetTCPConnection -OwningProcess $proc.Id -State Listen -ErrorAction SilentlyContinue | Select-Object -First 1
+    if ($conn) {
+        return $conn.LocalPort
+    }
+    return $null
+}
+
+function Test-Server {
+    param([string]$Server = "localhost", [int]$Port)
+    try {
+        $client = New-Object System.Net.Sockets.TcpClient
+        $asyncResult = $client.BeginConnect($Server, $Port, $null, $null)
+        if (-not $asyncResult.AsyncWaitHandle.WaitOne(1000)) {
+            $client.Close()
+            return $false
+        }
+        $client.EndConnect($asyncResult)
+        $stream = $client.GetStream()
+
+        $query = "?ping"
+        $queryBytes = [System.Text.Encoding]::ASCII.GetBytes($query)
+        $length = $queryBytes.Length + 6
+
+		# Byond topic packet construction
+        $packet = [byte[]]@(
+            0x00, 								 # Header byte
+            0x83, 								 # Header byte
+            [byte](($length -shr 8) -band 0xFF), # Message body size in big endian
+            [byte]($length -band 0xFF),		     # and lower byte, its an int16
+            0x00, 0x00, 0x00, 0x00, 0x00	     # flag, port (unused here so 0)
+        ) + $queryBytes + [byte]0x00			 # mesasge + null terminator
+
+        $stream.Write($packet, 0, $packet.Length)
+        $stream.Flush()
+        $stream.ReadTimeout = 1000
+
+        $buffer = New-Object byte[] 1024
+        $read = $stream.Read($buffer, 0, 1024)
+
+        $client.Close()
+        return $read -gt 0
+    } catch {
+        return $false
+    }
+}
+
+$detectedPort = $null
+
+while ($true) {
+	# get whatever port dreamdaemon is on
+    $port = Find-DreamDaemonPort
+    if ($port) {
+        Write-Host "Found DreamDaemon on port $port"
+		# ping the server to make sure we can actually connect yet
+        if (Test-Server -Port $port) {
+            $detectedPort = $port
+            break
+        }
+        Write-Host "Server is still starting and not responding yet, retrying"
+    } else {
+        Write-Host "DreamDaemon has not yet launched, retrying"
+    }
+    Start-Sleep -Seconds 2
+}
+
+if ($detectedPort) {
+    $dsPath = "C:\Program Files (x86)\BYOND\bin\dreamseeker.exe"
+    if (-not (Test-Path $dsPath)) {
+        $dsPath = "C:\Program Files\BYOND\bin\dreamseeker.exe"
+    }
+    Start-Process $dsPath -ArgumentList "byond://localhost:$detectedPort"
+}