diff --git a/vscode-wpilib/src/cpp/deploydebug.ts b/vscode-wpilib/src/cpp/deploydebug.ts
index e3976d19..ed4e51f7 100644
--- a/vscode-wpilib/src/cpp/deploydebug.ts
+++ b/vscode-wpilib/src/cpp/deploydebug.ts
@@ -10,8 +10,8 @@ import { IUnixSimulateCommands, startUnixSimulation } from './simulateunix';
 import { IWindowsSimulateCommands, startWindowsSimulation } from './simulatewindows';
 
 interface ICppDebugInfo {
-  debugfile: string;
-  artifact: string;
+  name: string;
+  path: string;
 }
 
 interface ICppSimExtensions {
@@ -26,7 +26,7 @@ interface ICppSimulateInfo {
   extensions: ICppSimExtensions[];
   launchfile: string;
   clang: boolean;
-  env?: Map<string, string>;
+  environment?: Map<string, string>;
   srcpaths: string[];
   headerpaths: string[];
   libpaths: string[];
@@ -34,18 +34,16 @@ interface ICppSimulateInfo {
 }
 
 interface ICppDebugCommand {
-  name?: string;
-  extensions: string;
-  clang?: boolean;
-  launchfile: string;
+  type: string;
+  name: string;
+  port: number;
   target: string;
+  launchfile: string;
   gdb: string;
-  env?: Map<string, string>;
-  sysroot: string | null;
+  sysroot: string | undefined;
   srcpaths: string[];
   headerpaths: string[];
   libpaths: string[];
-  debugpaths: string[];
   libsrcpaths: string[];
 }
 
@@ -91,10 +89,10 @@ class DebugCodeDeployer implements ICodeDeployer {
       return false;
     }
 
-    const debugInfo = await readFileAsync(path.join(workspace.uri.fsPath, 'build', 'debug', 'debuginfo.json'), 'utf8');
+    const debugInfo = await readFileAsync(path.join(workspace.uri.fsPath, 'build', 'debug', 'debug_info.json'), 'utf8');
     const parsedDebugInfo: ICppDebugInfo[] = jsonc.parse(debugInfo) as ICppDebugInfo[];
     if (parsedDebugInfo.length === 0) {
-      await vscode.window.showInformationMessage('No debug configurations found. Is this a robot project?', {
+      await vscode.window.showInformationMessage('No target configurations found. Is this a robot project?', {
         modal: true,
       });
       return false;
@@ -103,22 +101,46 @@ class DebugCodeDeployer implements ICodeDeployer {
     if (parsedDebugInfo.length > 1) {
       const arr: CppQuickPick<ICppDebugInfo>[] = [];
       for (const i of parsedDebugInfo) {
-        arr.push(new CppQuickPick<ICppDebugInfo>(i, i.artifact));
+        arr.push(new CppQuickPick<ICppDebugInfo>(i, i.name));
       }
       const picked = await vscode.window.showQuickPick(arr, {
-        placeHolder: 'Select an artifact',
+        placeHolder: 'Select a target',
       });
       if (picked === undefined) {
-        vscode.window.showInformationMessage('Artifact cancelled');
+        vscode.window.showInformationMessage('Target cancelled');
         return false;
       }
       targetDebugInfo = picked.debugInfo;
     }
 
-    const debugPath = path.join(workspace.uri.fsPath, 'build', 'debug', targetDebugInfo.debugfile);
+    const debugPath = targetDebugInfo.path;
 
     const targetReadInfo = await readFileAsync(debugPath, 'utf8');
-    const targetInfoParsed: ICppDebugCommand = jsonc.parse(targetReadInfo) as ICppDebugCommand;
+    const targetInfoArray: ICppDebugCommand[] = jsonc.parse(targetReadInfo) as ICppDebugCommand[];
+
+    if (targetInfoArray.length === 0) {
+      await vscode.window.showInformationMessage('No debug configurations found. Is this a robot project?', {
+        modal: true,
+      });
+      return false;
+    }
+
+    // TODO Filter this off of type
+    let targetInfoParsed = targetInfoArray[0];
+    if (targetInfoArray.length > 1) {
+      const arr: CppQuickPick<ICppDebugCommand>[] = [];
+      for (const i of targetInfoArray) {
+        arr.push(new CppQuickPick<ICppDebugCommand>(i, i.name));
+      }
+      const picked = await vscode.window.showQuickPick(arr, {
+        placeHolder: 'Select an artifact',
+      });
+      if (picked === undefined) {
+        vscode.window.showInformationMessage('Artifact cancelled');
+        return false;
+      }
+      targetInfoParsed = picked.debugInfo;
+    }
 
     const set = new Set<string>(targetInfoParsed.libpaths);
 
@@ -132,7 +154,7 @@ class DebugCodeDeployer implements ICodeDeployer {
 
     let sysroot = '';
 
-    if (targetInfoParsed.sysroot !== null) {
+    if (targetInfoParsed.sysroot !== undefined) {
       sysroot = targetInfoParsed.sysroot;
     }
 
@@ -147,7 +169,7 @@ class DebugCodeDeployer implements ICodeDeployer {
       soLibPath: soPath,
       srcPaths: new Set<string>(srcArrs),
       sysroot,
-      target: targetInfoParsed.target,
+      target: targetInfoParsed.target + ':' + targetInfoParsed.port.toString(10),
       workspace,
     };
 
@@ -291,7 +313,7 @@ class SimulateCodeDeployer implements ICodeDeployer {
 
       const config: IUnixSimulateCommands = {
         clang: targetSimulateInfo.clang,
-        environment: targetSimulateInfo.env,
+        environment: targetSimulateInfo.environment,
         executablePath: targetSimulateInfo.launchfile,
         extensions,
         ldPath: path.dirname(targetSimulateInfo.launchfile),    // gradle puts all the libs in the same dir as the executable
@@ -305,7 +327,7 @@ class SimulateCodeDeployer implements ICodeDeployer {
     } else {
       const config: IWindowsSimulateCommands = {
         debugPaths: targetSimulateInfo.libpaths,
-        environment: targetSimulateInfo.env,
+        environment: targetSimulateInfo.environment,
         extensions,
         launchfile: targetSimulateInfo.launchfile,
         srcPaths: targetSimulateInfo.srcpaths,
diff --git a/vscode-wpilib/src/java/deploydebug.ts b/vscode-wpilib/src/java/deploydebug.ts
index f790e718..7b094a27 100644
--- a/vscode-wpilib/src/java/deploydebug.ts
+++ b/vscode-wpilib/src/java/deploydebug.ts
@@ -9,14 +9,16 @@ import { IDebugCommands, startDebugging } from './debug';
 import { ISimulateCommands, startSimulation } from './simulate';
 
 interface IJavaDebugInfo {
-  debugfile: string;
-  project: string;
-  artifact: string;
+  name: string;
+  path: string;
 }
 
 interface ITargetInfo {
-  ipAddress: string;
-  port: string;
+  type: string;
+  name: string;
+  port: number;
+  target: string;
+  project: string;
 }
 
 interface IJavaSimExtensions {
@@ -29,7 +31,7 @@ interface IJavaSimulateInfo {
   name: string;
   type: string;
   extensions: IJavaSimExtensions[];
-  env?: Map<string, string>;
+  environment?: Map<string, string>;
   libraryDir: string;
   mainClassName: string;
 }
@@ -79,7 +81,7 @@ class DebugCodeDeployer implements ICodeDeployer {
       return false;
     }
 
-    const debugInfo = await readFileAsync(path.join(workspace.uri.fsPath, 'build', 'debug', 'debuginfo.json'), 'utf8');
+    const debugInfo = await readFileAsync(path.join(workspace.uri.fsPath, 'build', 'debug', 'debug_info.json'), 'utf8');
     const parsedDebugInfo: IJavaDebugInfo[] = jsonc.parse(debugInfo) as IJavaDebugInfo[];
     if (parsedDebugInfo.length === 0) {
       await vscode.window.showInformationMessage('No debug configurations found. Is this a robot project?', {
@@ -91,27 +93,51 @@ class DebugCodeDeployer implements ICodeDeployer {
     if (parsedDebugInfo.length > 1) {
       const arr: JavaQuickPick<IJavaDebugInfo>[] = [];
       for (const i of parsedDebugInfo) {
-        arr.push(new JavaQuickPick<IJavaDebugInfo>(i, i.artifact));
+        arr.push(new JavaQuickPick<IJavaDebugInfo>(i, i.name));
       }
       const picked = await vscode.window.showQuickPick(arr, {
-        placeHolder: 'Select an artifact',
+        placeHolder: 'Select a target',
       });
       if (picked === undefined) {
-        vscode.window.showInformationMessage('Artifact cancelled');
+        vscode.window.showInformationMessage('Target cancelled');
         return false;
       }
       targetDebugInfo = picked.debugInfo;
     }
 
-    const debugPath = path.join(workspace.uri.fsPath, 'build', 'debug', targetDebugInfo.debugfile);
+    const debugPath = targetDebugInfo.path;
 
     const targetReadInfo = await readFileAsync(debugPath, 'utf8');
-    const targetInfoParsed = jsonc.parse(targetReadInfo) as ITargetInfo;
+    const targetInfoArray = jsonc.parse(targetReadInfo) as ITargetInfo[];
+
+    if (targetInfoArray.length === 0) {
+      await vscode.window.showInformationMessage('No debug configurations found. Is this a robot project?', {
+        modal: true,
+      });
+      return false;
+    }
+
+    // TODO Filter this off of type
+    let targetInfoParsed = targetInfoArray[0];
+    if (targetInfoArray.length > 1) {
+      const arr: JavaQuickPick<ITargetInfo>[] = [];
+      for (const i of targetInfoArray) {
+        arr.push(new JavaQuickPick<ITargetInfo>(i, i.name));
+      }
+      const picked = await vscode.window.showQuickPick(arr, {
+        placeHolder: 'Select an artifact',
+      });
+      if (picked === undefined) {
+        vscode.window.showInformationMessage('Artifact cancelled');
+        return false;
+      }
+      targetInfoParsed = picked.debugInfo;
+    }
 
     const config: IDebugCommands = {
-      project: targetDebugInfo.project,
-      serverAddress: targetInfoParsed.ipAddress,
-      serverPort: targetInfoParsed.port,
+      project: targetInfoParsed.project,
+      serverAddress: targetInfoParsed.target,
+      serverPort: targetInfoParsed.port.toString(10),
       workspace,
     };
 
@@ -246,7 +272,7 @@ class SimulateCodeDeployer implements ICodeDeployer {
     }
 
     const config: ISimulateCommands = {
-      environment: targetSimulateInfo.env,
+      environment: targetSimulateInfo.environment,
       extensions,
       librarydir: targetSimulateInfo.libraryDir,
       mainclass: targetSimulateInfo.mainClassName,