diff --git a/npm-shrinkwrap.json b/npm-shrinkwrap.json
index d5c1fecae..a94440844 100644
--- a/npm-shrinkwrap.json
+++ b/npm-shrinkwrap.json
@@ -29,7 +29,7 @@
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-        "lando": "github:automattic/lando-cli#bff037ea318948a1bac623c12ede017928cb99db",
+        "lando": "github:automattic/lando-cli#8f198e0f17dec1144efa216bec5a227dfc851900",
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@@ -2545,10 +2545,30 @@
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       }
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+      "resolved": "https://registry.npmjs.org/@isaacs/balanced-match/-/balanced-match-4.0.1.tgz",
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+      "dev": true,
       "license": "ISC",
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+      "dev": true,
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@@ -9643,6 +9649,7 @@
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+      "dev": true,
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@@ -11297,8 +11304,8 @@
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+      "resolved": "git+ssh://git@github.com/automattic/lando-cli.git#8f198e0f17dec1144efa216bec5a227dfc851900",
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@@ -11307,19 +11314,16 @@
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         "copy-dir": "^1.3.0",
         "dockerode": "^4.0.9",
-        "figlet": "^1.9.4",
-        "glob": "^10.5.0",
+        "glob": "^13.0.0",
         "js-yaml": "^4.1.1",
         "jsonfile": "^6.1.0",
         "lodash": "^4.17.21",
         "node-cache": "^5.1.2",
-        "object-hash": "^1.1.8",
+        "object-hash": "^3.0.0",
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-      "license": "ISC",
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+      "resolved": "https://registry.npmjs.org/glob/-/glob-13.0.0.tgz",
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-        "foreground-child": "^3.1.0",
-        "jackspeak": "^3.1.2",
-        "minimatch": "^9.0.4",
+        "minimatch": "^10.1.1",
         "minipass": "^7.1.2",
-        "package-json-from-dist": "^1.0.0",
-        "path-scurry": "^1.11.1"
+        "path-scurry": "^2.0.0"
       },
-      "bin": {
-        "glob": "dist/esm/bin.mjs"
+      "engines": {
+        "node": "20 || >=22"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/isaacs"
+      }
+    },
+    "node_modules/lando/node_modules/lru-cache": {
+      "version": "11.2.4",
+      "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-11.2.4.tgz",
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+      "engines": {
+        "node": "20 || >=22"
+      }
+    },
+    "node_modules/lando/node_modules/minimatch": {
+      "version": "10.1.1",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.1.1.tgz",
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+      },
+      "engines": {
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-      "license": "ISC",
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       }
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+    "node_modules/lando/node_modules/path-scurry": {
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+      "resolved": "https://registry.npmjs.org/path-scurry/-/path-scurry-2.0.1.tgz",
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+        "minipass": "^7.1.2"
+      },
+      "engines": {
+        "node": "20 || >=22"
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+      "funding": {
+        "url": "https://github.com/sponsors/isaacs"
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+        "node": ">= 6"
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       "version": "2.0.1",
       "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-2.0.1.tgz",
       "integrity": "sha512-RRECPsj7iu/xb5oKYcsFHSppFNnsj/52OVTRKb4zP5onXwVF3zVmmToNcOfGC+CRDpfK/U584fMg38ZHCaElKQ==",
+      "dev": true,
       "license": "MIT",
       "dependencies": {
         "color-name": "~1.1.4"
@@ -15233,6 +15268,7 @@
       "version": "1.1.4",
       "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.4.tgz",
       "integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==",
+      "dev": true,
       "license": "MIT"
     },
     "node_modules/wrap-ansi/node_modules/ansi-regex": {
diff --git a/package.json b/package.json
index a59bf345e..6bd0950af 100644
--- a/package.json
+++ b/package.json
@@ -157,7 +157,7 @@
     "https-proxy-agent": "^7.0.6",
     "js-yaml": "^4.1.0",
     "jwt-decode": "4.0.0",
-    "lando": "github:automattic/lando-cli#bff037ea318948a1bac623c12ede017928cb99db",
+    "lando": "github:automattic/lando-cli#459ac2d44ac3db17719493e879d52178410ff70e",
     "node-fetch": "^3.3.2",
     "node-stream-zip": "1.15.0",
     "open": "^11.0.0",
diff --git a/src/bin/vip-dev-env-create.js b/src/bin/vip-dev-env-create.js
index c5c9cbe4b..ef3621396 100755
--- a/src/bin/vip-dev-env-create.js
+++ b/src/bin/vip-dev-env-create.js
@@ -17,6 +17,7 @@ import {
 	processStringOrBooleanOption,
 	processSlug,
 	ensureValidPathsInOptions,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import {
 	getConfigurationFileOptions,
@@ -102,7 +103,7 @@ cmd.argv( process.argv, async ( arg, opt ) => {
 		slug = await getEnvironmentName( environmentNameOptions );
 	}
 
-	const lando = await bootstrapLando();
+	const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 	validateDependencies( lando );
 
 	debug( 'Args: ', arg, 'Options: ', opt );
diff --git a/src/bin/vip-dev-env-destroy.js b/src/bin/vip-dev-env-destroy.js
index 396f35fb4..45f604d42 100755
--- a/src/bin/vip-dev-env-destroy.js
+++ b/src/bin/vip-dev-env-destroy.js
@@ -10,6 +10,7 @@ import {
 	handleCLIException,
 	processSlug,
 	validateDependencies,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { destroyEnvironment } from '../lib/dev-environment/dev-environment-core';
 import { bootstrapLando } from '../lib/dev-environment/dev-environment-lando';
@@ -50,7 +51,7 @@ command( {
 	.argv( process.argv, async ( arg, opt ) => {
 		const slug = await getEnvironmentName( opt );
 
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 		validateDependencies( lando );
 
 		const trackingInfo = getEnvTrackingInfo( slug );
diff --git a/src/bin/vip-dev-env-exec.js b/src/bin/vip-dev-env-exec.js
index 136d60b7d..deae0cb85 100755
--- a/src/bin/vip-dev-env-exec.js
+++ b/src/bin/vip-dev-env-exec.js
@@ -8,6 +8,7 @@ import {
 	processBooleanOption,
 	processSlug,
 	validateDependencies,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { exec, getEnvironmentPath } from '../lib/dev-environment/dev-environment-core';
 import { bootstrapLando, isEnvUp } from '../lib/dev-environment/dev-environment-lando';
@@ -56,7 +57,7 @@ command( {
 	.examples( examples )
 	.argv( process.argv, async ( unmatchedArgs, opt ) => {
 		const slug = await getEnvironmentName( opt );
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 		validateDependencies( lando );
 
 		const trackingInfo = getEnvTrackingInfo( slug );
diff --git a/src/bin/vip-dev-env-info.js b/src/bin/vip-dev-env-info.js
index 17ef2f097..62736d259 100755
--- a/src/bin/vip-dev-env-info.js
+++ b/src/bin/vip-dev-env-info.js
@@ -9,6 +9,7 @@ import {
 	handleCLIException,
 	processSlug,
 	validateDependencies,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import {
 	printEnvironmentInfo,
@@ -47,16 +48,16 @@ command( {
 	.argv( process.argv, async ( arg, opt ) => {
 		let trackingInfo;
 		let slug;
-		const lando = await bootstrapLando();
 
 		if ( opt.all ) {
 			trackingInfo = { all: true };
-			slug = '';
+			slug = undefined;
 		} else {
 			slug = await getEnvironmentName( opt );
 			trackingInfo = getEnvTrackingInfo( slug );
 		}
 
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 		validateDependencies( lando );
 		await trackEvent( 'dev_env_info_command_execute', trackingInfo );
 
diff --git a/src/bin/vip-dev-env-list.js b/src/bin/vip-dev-env-list.js
index 1522446b5..e0ef46dfd 100755
--- a/src/bin/vip-dev-env-list.js
+++ b/src/bin/vip-dev-env-list.js
@@ -4,6 +4,7 @@ import command from '../lib/cli/command';
 import {
 	handleCLIException,
 	validateDependencies,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { printAllEnvironmentsInfo } from '../lib/dev-environment/dev-environment-core';
 import { bootstrapLando } from '../lib/dev-environment/dev-environment-lando';
@@ -24,7 +25,7 @@ command( {
 } )
 	.examples( examples )
 	.argv( process.argv, async () => {
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile() } );
 		lando.events.constructor.prototype.setMaxListeners( 1024 );
 		validateDependencies( lando );
 
diff --git a/src/bin/vip-dev-env-logs.js b/src/bin/vip-dev-env-logs.js
index 5bf7a34ed..7ebdf1a28 100755
--- a/src/bin/vip-dev-env-logs.js
+++ b/src/bin/vip-dev-env-logs.js
@@ -9,6 +9,7 @@ import {
 	handleCLIException,
 	processSlug,
 	validateDependencies,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { showLogs } from '../lib/dev-environment/dev-environment-core';
 import { bootstrapLando } from '../lib/dev-environment/dev-environment-lando';
@@ -51,7 +52,7 @@ command( {
 	.argv( process.argv, async ( arg, opt ) => {
 		const slug = await getEnvironmentName( opt );
 
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 		validateDependencies( lando );
 
 		const trackingInfo = getEnvTrackingInfo( slug );
diff --git a/src/bin/vip-dev-env-purge.js b/src/bin/vip-dev-env-purge.js
index e3c012441..171ebe03c 100755
--- a/src/bin/vip-dev-env-purge.js
+++ b/src/bin/vip-dev-env-purge.js
@@ -15,6 +15,7 @@ import {
 	handleCLIException,
 	validateDependencies,
 	promptForBoolean,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import {
 	destroyEnvironment,
@@ -57,7 +58,7 @@ command( {
 		debug( 'Args: ', arg, 'Options: ', opt );
 
 		const allEnvNames = getAllEnvironmentNames();
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile() } );
 
 		if ( allEnvNames.length === 0 ) {
 			console.log( 'No environments to purge!' );
diff --git a/src/bin/vip-dev-env-shell.js b/src/bin/vip-dev-env-shell.js
index bb79a8689..eb0aa0dbd 100755
--- a/src/bin/vip-dev-env-shell.js
+++ b/src/bin/vip-dev-env-shell.js
@@ -9,6 +9,7 @@ import {
 	getEnvironmentName,
 	handleCLIException,
 	processSlug,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { getEnvironmentPath } from '../lib/dev-environment/dev-environment-core';
 import { bootstrapLando, landoShell } from '../lib/dev-environment/dev-environment-lando';
@@ -90,7 +91,7 @@ command( {
 	.argv( process.argv, async ( args, opt ) => {
 		const slug = await getEnvironmentName( opt );
 
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 		validateDependencies( lando );
 
 		const trackingInfo = getEnvTrackingInfo( slug );
diff --git a/src/bin/vip-dev-env-start.js b/src/bin/vip-dev-env-start.js
index 699143a4f..476b37c0b 100755
--- a/src/bin/vip-dev-env-start.js
+++ b/src/bin/vip-dev-env-start.js
@@ -10,6 +10,7 @@ import {
 	handleCLIException,
 	postStart,
 	processSlug,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { startEnvironment } from '../lib/dev-environment/dev-environment-core';
 import { bootstrapLando } from '../lib/dev-environment/dev-environment-lando';
@@ -76,7 +77,7 @@ command( {
 	.examples( examples )
 	.argv( process.argv, async ( arg, opt ) => {
 		const slug = await getEnvironmentName( opt );
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 		validateDependencies( lando );
 
 		const startProcessing = new Date();
diff --git a/src/bin/vip-dev-env-stop.js b/src/bin/vip-dev-env-stop.js
index 6f9ad9029..a5a6cbeb2 100755
--- a/src/bin/vip-dev-env-stop.js
+++ b/src/bin/vip-dev-env-stop.js
@@ -9,6 +9,7 @@ import {
 	getEnvironmentName,
 	processSlug,
 	validateDependencies,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import {
 	getAllEnvironmentNames,
@@ -44,24 +45,28 @@ command( {
 	.option( 'all', 'Stop all local environments.' )
 	.examples( examples )
 	.argv( process.argv, async ( arg, opt ) => {
-		const lando = await bootstrapLando();
-		validateDependencies( lando );
-
 		debug( 'Args: ', arg, 'Options: ', opt );
 
 		/** @type {Record< string, unknown >} */
 		let trackingInfo;
 		/** @type {string[]} */
 		let environments;
+		/** @type {string|undefined} */
+		let logSlug;
 		if ( opt.all ) {
 			trackingInfo = { all: true };
 			environments = getAllEnvironmentNames();
+			logSlug = undefined;
 		} else {
 			const slug = await getEnvironmentName( opt );
 			trackingInfo = getEnvTrackingInfo( slug );
 			environments = [ slug ];
+			logSlug = slug;
 		}
 
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( logSlug ) } );
+		validateDependencies( lando );
+
 		await trackEvent( 'dev_env_stop_command_execute', trackingInfo );
 
 		for ( const slug of environments ) {
diff --git a/src/bin/vip-dev-env-sync-sql.js b/src/bin/vip-dev-env-sync-sql.js
index dc06728ce..3b1bdeeaf 100755
--- a/src/bin/vip-dev-env-sync-sql.js
+++ b/src/bin/vip-dev-env-sync-sql.js
@@ -6,6 +6,7 @@ import {
 	getEnvironmentName,
 	processBooleanOption,
 	processSlug,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import { bootstrapLando, isContainerRunning } from '../lib/dev-environment/dev-environment-lando';
 import { parseLiveBackupCopyCLIOptions } from '../lib/live-backup-copy';
@@ -114,7 +115,7 @@ command( {
 		} );
 		await trackerFn( 'execute' );
 
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 
 		const isUp = (
 			await Promise.all( [
diff --git a/src/bin/vip-dev-env-update.js b/src/bin/vip-dev-env-update.js
index 0ca13c50e..2c6085f83 100755
--- a/src/bin/vip-dev-env-update.js
+++ b/src/bin/vip-dev-env-update.js
@@ -17,6 +17,7 @@ import {
 	promptForArguments,
 	validateDependencies,
 	ensureValidPathsInOptions,
+	getDevEnvLogFile,
 } from '../lib/dev-environment/dev-environment-cli';
 import {
 	getConfigurationFileOptions,
@@ -68,7 +69,7 @@ cmd.examples( examples );
 cmd.argv( process.argv, async ( arg, opt ) => {
 	const slug = await getEnvironmentName( opt );
 
-	const lando = await bootstrapLando();
+	const lando = await bootstrapLando( { logFile: getDevEnvLogFile( slug ) } );
 	validateDependencies( lando );
 
 	const trackingInfo = getEnvTrackingInfo( slug );
diff --git a/src/commands/dev-env-import-sql.ts b/src/commands/dev-env-import-sql.ts
index 23317fb3e..d27685cfb 100644
--- a/src/commands/dev-env-import-sql.ts
+++ b/src/commands/dev-env-import-sql.ts
@@ -6,6 +6,7 @@ import * as exit from '../lib/cli/exit';
 import { getFileMeta, unzipFile } from '../lib/client-file-uploader';
 import { getSqlDumpDetails, SqlDumpDetails, SqlDumpType } from '../lib/database';
 import {
+	getDevEnvLogFile,
 	processBooleanOption,
 	validateDependencies,
 } from '../lib/dev-environment/dev-environment-cli';
@@ -39,7 +40,7 @@ export class DevEnvImportSQLCommand {
 	) {}
 
 	public async run(): Promise< void > {
-		const lando = await bootstrapLando();
+		const lando = await bootstrapLando( { logFile: getDevEnvLogFile( this.slug ) } );
 		validateDependencies( lando );
 
 		validateImportFileExtension( this.fileName );
diff --git a/src/lib/dev-environment/dev-environment-cli.ts b/src/lib/dev-environment/dev-environment-cli.ts
index 69a0285f9..c9d3c97d6 100644
--- a/src/lib/dev-environment/dev-environment-cli.ts
+++ b/src/lib/dev-environment/dev-environment-cli.ts
@@ -954,6 +954,19 @@ export function processSlug( value: unknown ): string {
 	return ( value ?? '' ).toString().toLowerCase();
 }
 
+export function formatDevEnvLogTimestamp( date: Date ): string {
+	return date.toISOString().replace( /\..*$/, '' ).replace( /[-:]/g, '' ).replace( 'T', '-' );
+}
+
+export function formatDevEnvLogSlug( slug: string ): string {
+	return slug.replace( /[^a-z0-9_-]+/gi, '-' ).toLowerCase();
+}
+
+export function getDevEnvLogFile( slug?: string ): string {
+	const slugPart = slug ? formatDevEnvLogSlug( slug ) : 'all';
+	return `vip-dev-env-${ slugPart }-${ formatDevEnvLogTimestamp( new Date() ) }.log`;
+}
+
 declare function isNaN( value: unknown ): boolean;
 declare function parseFloat( value: unknown ): number;
 
diff --git a/src/lib/dev-environment/dev-environment-lando.ts b/src/lib/dev-environment/dev-environment-lando.ts
index 1dbdad690..aae3dcdca 100644
--- a/src/lib/dev-environment/dev-environment-lando.ts
+++ b/src/lib/dev-environment/dev-environment-lando.ts
@@ -6,10 +6,12 @@ import { buildConfig } from 'lando/lib/bootstrap';
 import Lando, { type LandoConfig } from 'lando/lib/lando';
 import landoUtils, { type AppInfo } from 'lando/plugins/lando-core/lib/utils';
 import landoBuildTask from 'lando/plugins/lando-tooling/lib/build';
+import { execFile } from 'node:child_process';
 import { lookup } from 'node:dns/promises';
-import { mkdir, rename, unlink } from 'node:fs/promises';
-import { userInfo } from 'node:os';
+import { mkdir, rename, unlink, stat, writeFile } from 'node:fs/promises';
+import { cpus, totalmem, userInfo } from 'node:os';
 import path, { dirname } from 'node:path';
+import { promisify } from 'node:util';
 import { satisfies } from 'semver';
 
 import {
@@ -21,6 +23,7 @@ import {
 } from './dev-environment-core';
 import { getDockerSocket, getEngineConfig } from './docker-utils';
 import { DEV_ENVIRONMENT_NOT_FOUND } from '../constants/dev-environment';
+import env from '../env';
 import UserError from '../user-error';
 import { xdgData } from '../xdg-data';
 
@@ -38,10 +41,179 @@ export interface LandoExecOptions {
 const DEBUG_KEY = '@automattic/vip:bin:dev-environment';
 const debug = debugLib( DEBUG_KEY );
 
+interface LandoBootstrapOptions {
+	logFile?: string;
+	logName?: string;
+}
+
+interface LandoConfigWithLogging extends Omit< LandoConfig, 'composeBin' | 'dockerBin' > {
+	logFile?: string;
+	logName?: string;
+	logDir?: string;
+	dockerBin?: string;
+	composeBin?: string;
+}
+
+const execFileAsync = promisify( execFile );
+const bannerLabelWidth = 18;
+let logPathRegistered = false;
+let resolvedLogPath: string | null = null;
+
+const getLogFilePath = ( config: LandoConfigWithLogging ): string | null => {
+	if ( config.logFile ) {
+		return path.isAbsolute( config.logFile )
+			? config.logFile
+			: path.join( config.logDir ?? '', config.logFile );
+	}
+
+	if ( config.logDir && config.logName ) {
+		return path.join( config.logDir, `${ config.logName }.log` );
+	}
+
+	return null;
+};
+
+const registerLogPathOutput = ( config: LandoConfigWithLogging ): void => {
+	if ( logPathRegistered ) {
+		return;
+	}
+
+	resolvedLogPath = getLogFilePath( config );
+	if ( ! resolvedLogPath ) {
+		return;
+	}
+
+	logPathRegistered = true;
+	process.once( 'exit', () => {
+		if ( resolvedLogPath && process.stdout.isTTY ) {
+			console.log(
+				`\n ${ formatBannerLine(
+					chalk.cyan( 'COMMAND LOG FILE'.padEnd( bannerLabelWidth ) ),
+					resolvedLogPath
+				) }`
+			);
+		}
+	} );
+};
+
+const formatBytes = ( bytes: number ): string => {
+	const gb = bytes / 1024 ** 3;
+	return `${ gb.toFixed( 1 ) } GB`;
+};
+
+type DockerPluginInfo = {
+	Name?: string;
+	Version?: string;
+};
+
+type DockerClientInfo = {
+	Plugins?: DockerPluginInfo[];
+};
+
+type DockerInfo = {
+	ServerVersion?: string;
+	ClientInfo?: DockerClientInfo;
+};
+
+const isRecord = ( value: unknown ): value is Record< string, unknown > =>
+	typeof value === 'object' && value !== null;
+
+const isDockerPluginInfo = ( value: unknown ): value is DockerPluginInfo => isRecord( value );
+
+const getDockerVersions = async ( config: LandoConfigWithLogging ) => {
+	const dockerBin = config.dockerBin ?? '';
+	const composeBin = config.composeBin ?? '';
+	let engine = 'unknown';
+	let compose = 'unknown';
+	let composePlugin = 'unknown';
+
+	try {
+		if ( dockerBin ) {
+			const { stdout } = await execFileAsync( dockerBin, [ 'info', '--format', 'json' ] );
+			const dockerData = JSON.parse( stdout ) as DockerInfo;
+			if ( isRecord( dockerData ) ) {
+				const serverVersion = dockerData.ServerVersion;
+				if ( typeof serverVersion === 'string' ) {
+					engine = serverVersion;
+				}
+
+				const clientInfo = dockerData.ClientInfo;
+				if ( isRecord( clientInfo ) ) {
+					const plugins = clientInfo.Plugins;
+					if ( Array.isArray( plugins ) ) {
+						const composePluginEntry = plugins.find(
+							plugin => isDockerPluginInfo( plugin ) && plugin.Name === 'compose'
+						);
+						if ( composePluginEntry && typeof composePluginEntry.Version === 'string' ) {
+							composePlugin = composePluginEntry.Version;
+						}
+					}
+				}
+			}
+		}
+	} catch ( error ) {
+		debug( 'Failed to read docker version info: %O', error );
+	}
+
+	try {
+		if ( composeBin ) {
+			const { stdout } = await execFileAsync( composeBin, [ 'version', '--short' ] );
+			compose = stdout.trim() || compose;
+		}
+	} catch ( error ) {
+		debug( 'Failed to read docker-compose version info: %O', error );
+	}
+
+	return { engine, compose, composePlugin };
+};
+
+const formatBannerLine = ( label: string, value: string ): string =>
+	`${ label.padEnd( bannerLabelWidth ) } ${ value }`;
+
+const writeLogBanner = async ( config: LandoConfigWithLogging ): Promise< void > => {
+	const logFilePath = getLogFilePath( config );
+	if ( ! logFilePath ) {
+		return;
+	}
+
+	try {
+		const existing = await stat( logFilePath );
+		if ( existing.size > 0 ) {
+			return;
+		}
+	} catch {
+		// File does not exist yet.
+	}
+
+	await mkdir( path.dirname( logFilePath ), { recursive: true } );
+
+	const dockerVersions = await getDockerVersions( config );
+	const command = process.argv.slice( 1 ).join( ' ' );
+	const bannerLines = [
+		'=== VIP Dev Env Log ===',
+		formatBannerLine( 'COMMAND', command ),
+		formatBannerLine( 'OS', `${ env.os.name } ${ env.os.version } ${ env.os.arch }` ),
+		formatBannerLine( 'NODE', env.node.version ),
+		formatBannerLine( 'VIP-CLI', env.app.version ),
+		formatBannerLine( 'DOCKER ENGINE', dockerVersions.engine ),
+		formatBannerLine( 'DOCKER COMPOSE', dockerVersions.compose ),
+		formatBannerLine( 'COMPOSE PLUGIN', dockerVersions.composePlugin ),
+		formatBannerLine( 'DOCKER BIN', config.dockerBin ?? 'unknown' ),
+		formatBannerLine( 'COMPOSE BIN', config.composeBin ?? 'unknown' ),
+		formatBannerLine( 'RAM', formatBytes( totalmem() ) ),
+		formatBannerLine( 'CPU', String( cpus().length ) ),
+		'===',
+		'',
+		'',
+	];
+
+	await writeFile( logFilePath, bannerLines.join( '\n' ), { flag: 'a' } );
+};
+
 /**
  * @return {Promise<LandoConfig>} Lando configuration
  */
-async function getLandoConfig(): Promise< LandoConfig > {
+async function getLandoConfig( options: LandoBootstrapOptions = {} ): Promise< LandoConfig > {
 	// The path will be smth like `yarn/global/node_modules/lando/lib/lando.js`; we need the path up to `lando` (inclusive)
 	const landoPath = dirname( dirname( require.resolve( 'lando' ) ) );
 
@@ -61,6 +233,7 @@ async function getLandoConfig(): Promise< LandoConfig > {
 	const vipDir = path.join( xdgData(), 'vip' );
 	const landoDir = path.join( vipDir, 'lando' );
 	const fakeHomeDir = path.join( landoDir, 'home' );
+	const logDir = path.join( landoDir, 'logs' );
 
 	try {
 		await mkdir( fakeHomeDir, { recursive: true } );
@@ -70,6 +243,9 @@ async function getLandoConfig(): Promise< LandoConfig > {
 
 	const config = {
 		logLevelConsole,
+		logDir,
+		logFile: options.logFile ?? 'vip-dev-env.log',
+		logName: options.logName ?? 'vip-dev-env',
 		configSources: [ path.join( landoDir, 'config.yml' ) ],
 		landoFile: '.lando.yml',
 		preLandoFiles: [ '.lando.base.yml', '.lando.dist.yml', '.lando.upstream.yml' ],
@@ -187,11 +363,15 @@ async function getLandoApplication( lando: Lando, instancePath: string ): Promis
 	}
 }
 
-export async function bootstrapLando(): Promise< Lando > {
+export async function bootstrapLando( options: LandoBootstrapOptions = {} ): Promise< Lando > {
 	const started = new Date();
 	try {
+		if ( process.env.DEBUG && ! process.env.DEBUG.includes( '-winston:*' ) ) {
+			process.env.DEBUG = `${ process.env.DEBUG },-winston:*`;
+		}
+
 		const socket = await getDockerSocket();
-		const config = await getLandoConfig();
+		const config = await getLandoConfig( options );
 
 		debug( 'Docker socket: %j', socket );
 
@@ -200,7 +380,13 @@ export async function bootstrapLando(): Promise< Lando > {
 			debug( 'Engine config: %j', config.engineConfig );
 		}
 
+		registerLogPathOutput( config as LandoConfigWithLogging );
+		await writeLogBanner( config as LandoConfigWithLogging );
+
 		const lando = new Lando( config );
+		debugLib.log = ( message: string, ...args: unknown[] ) => {
+			lando.log.debug( message, ...args );
+		};
 		lando.events.once( 'pre-engine-build', async ( data: App ) => {
 			const instanceData = readEnvironmentData( data.name );
 
diff --git a/types/lando/lib/logger.d.ts b/types/lando/lib/logger.d.ts
index 32bdd8a66..108a27cc1 100644
--- a/types/lando/lib/logger.d.ts
+++ b/types/lando/lib/logger.d.ts
@@ -3,15 +3,20 @@ export = Log;
 declare class Log extends winston.Logger {
 	constructor( {
 		logDir,
+		logFile,
 		logLevelConsole,
 		logLevel,
 		logName,
+		logger,
 	}?: {
 		logDir: any;
+		logFile?: string;
 		logLevelConsole?: string;
 		logLevel?: string;
 		logName?: string;
+		logger?: winston.Logger;
 	} );
 	sanitizedKeys: string[];
 	alsoSanitize( key: any ): void;
+	child( logName: string ): Log;
 }