diff --git a/src/integrations/terminal/Terminal.ts b/src/integrations/terminal/Terminal.ts
index 8bf2072f3d49..6f2cf98cccc8 100644
--- a/src/integrations/terminal/Terminal.ts
+++ b/src/integrations/terminal/Terminal.ts
@@ -9,6 +9,8 @@ import { mergePromise } from "./mergePromise"
 
 export class Terminal extends BaseTerminal {
 	public terminal: vscode.Terminal
+	private isNewlyCreated: boolean = false
+	private firstCommandExecuted: boolean = false
 
 	public cmdCounter: number = 0
 
@@ -19,6 +21,9 @@ export class Terminal extends BaseTerminal {
 		const iconPath = new vscode.ThemeIcon("rocket")
 		this.terminal = terminal ?? vscode.window.createTerminal({ cwd, name: "Roo Code", iconPath, env })
 
+		// Mark if this is a newly created terminal
+		this.isNewlyCreated = terminal === undefined
+
 		if (Terminal.getTerminalZdotdir()) {
 			ShellIntegrationManager.terminalTmpDirs.set(id, env.ZDOTDIR)
 		}
@@ -71,10 +76,24 @@ export class Terminal extends BaseTerminal {
 			pWaitFor(() => this.terminal.shellIntegration !== undefined, {
 				timeout: Terminal.getShellIntegrationTimeout(),
 			})
-				.then(() => {
+				.then(async () => {
 					// Clean up temporary directory if shell integration is available, zsh did its job:
 					ShellIntegrationManager.zshCleanupTmpDir(this.id)
 
+					// For newly created terminals on the first command, add a small delay
+					// to ensure the shell integration stream is fully ready.
+					// This addresses a race condition where the first command's output might not
+					// be captured properly, especially with chained commands like "ENV=hello && echo $ENV".
+					// The 200ms delay was chosen empirically to balance between:
+					// - Giving enough time for shell integration to fully initialize
+					// - Not adding noticeable latency to command execution
+					// This may need adjustment for slower systems or different shells.
+					if (this.isNewlyCreated && !this.firstCommandExecuted) {
+						console.log(`[Terminal ${this.id}] Adding delay for first command in new terminal`)
+						await new Promise((resolve) => setTimeout(resolve, 200))
+						this.firstCommandExecuted = true
+					}
+
 					// Run the command in the terminal
 					process.run(command)
 				})
diff --git a/src/integrations/terminal/TerminalProcess.ts b/src/integrations/terminal/TerminalProcess.ts
index eb0424fe8df6..2d142286de12 100644
--- a/src/integrations/terminal/TerminalProcess.ts
+++ b/src/integrations/terminal/TerminalProcess.ts
@@ -158,6 +158,7 @@ export class TerminalProcess extends BaseTerminalProcess {
 
 		let preOutput = ""
 		let commandOutputStarted = false
+		let chunksReceived = 0
 
 		/*
 		 * Extract clean output from raw accumulated output. FYI:
@@ -171,6 +172,8 @@ export class TerminalProcess extends BaseTerminalProcess {
 
 		// Process stream data
 		for await (let data of stream) {
+			chunksReceived++
+
 			// Check for command output start marker
 			if (!commandOutputStarted) {
 				preOutput += data
@@ -182,7 +185,26 @@ export class TerminalProcess extends BaseTerminalProcess {
 					this.fullOutput = "" // Reset fullOutput when command actually starts
 					this.emit("line", "") // Trigger UI to proceed
 				} else {
-					continue
+					// For the first few chunks, wait to see if markers arrive
+					// This handles cases where markers might be split across chunks
+					if (chunksReceived < 3 && preOutput.length < 100) {
+						continue
+					}
+					// If we have accumulated enough preOutput without finding markers,
+					// treat it as command output to avoid losing data
+					// 500 chars threshold chosen to balance between waiting for markers
+					// and not losing legitimate output from fast commands
+					if (preOutput.length > 500) {
+						console.warn(
+							`[Terminal Process] No start markers found after ${preOutput.length} chars, treating as output`,
+						)
+						commandOutputStarted = true
+						data = preOutput
+						this.fullOutput = ""
+						this.emit("line", "")
+					} else {
+						continue
+					}
 				}
 			}