diff --git a/docs/CHANGELOG.md b/docs/CHANGELOG.md
index 1936d445a6..7d5915a895 100644
--- a/docs/CHANGELOG.md
+++ b/docs/CHANGELOG.md
@@ -1,5 +1,20 @@
 ## Changelog
 
+### 2.39.7
+
+* Fix promptForBoolean to display the default initial value capitalized
+* fix(dev-env): `vip dev-env info --all` should not ask for a slug
+* build(deps-dev): bump rimraf from 5.0.5 to 5.0.7
+* build(deps): bump cli-table3 from 0.6.4 to 0.6.5
+* build(deps): bump semver from 7.6.0 to 7.6.2
+* build(deps-dev): bump @types/node from 18.19.31 to 18.19.33
+* build(deps-dev): bump @automattic/eslint-plugin-wpvip from 0.9.1 to 0.10/1832
+* build(deps-dev): bump @automattic/eslint-plugin-wpvip from 0.10.0 to 0.11l/1835
+* fix(dev-env): plugin loading when using yarn to install VIP CLI
+* feat(dev-env): track versions of `docker` and `docker-compose`
+
+**Full Changelog**: https://github.com/Automattic/vip-cli/compare/2.39.6...2.39.7
+
 ### 2.39.6
 * Custom Deploys: Update deploy validation to run fully off of the custom deploy token. There are breaking changes associated with these updates, so the VIP CLI must be updated to this latest version in order to continue using the custom deploy functionality.
 
diff --git a/npm-shrinkwrap.json b/npm-shrinkwrap.json
index 69a1b1cc6b..51e9eb2ac2 100644
--- a/npm-shrinkwrap.json
+++ b/npm-shrinkwrap.json
@@ -1,12 +1,12 @@
 {
   "name": "@automattic/vip",
-  "version": "2.39.7-dev.0",
+  "version": "2.39.8-dev.0",
   "lockfileVersion": 2,
   "requires": true,
   "packages": {
     "": {
       "name": "@automattic/vip",
-      "version": "2.39.7-dev.0",
+      "version": "2.39.8-dev.0",
       "hasInstallScript": true,
       "license": "MIT",
       "dependencies": {
@@ -35,7 +35,7 @@
         "node-fetch": "^2.6.1",
         "open": "^10.0.0",
         "proxy-from-env": "^1.1.0",
-        "semver": "7.6.0",
+        "semver": "7.6.2",
         "shelljs": "^0.8.5",
         "single-line-log": "1.1.2",
         "socket.io-client": "^4.5.3",
@@ -105,7 +105,7 @@
         "vip-wp": "dist/bin/vip-wp.js"
       },
       "devDependencies": {
-        "@automattic/eslint-plugin-wpvip": "0.9.1",
+        "@automattic/eslint-plugin-wpvip": "0.11.0",
         "@babel/cli": "7.24.5",
         "@babel/core": "7.24.5",
         "@babel/preset-env": "7.24.5",
@@ -134,7 +134,7 @@
         "jest": "^29.7.0",
         "nock": "13.5.4",
         "prettier": "npm:wp-prettier@2.8.5",
-        "rimraf": "5.0.5",
+        "rimraf": "5.0.7",
         "typescript": "^5.2.2"
       },
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@@ -201,19 +201,19 @@
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+      "version": "0.11.0",
+      "resolved": "https://registry.npmjs.org/@automattic/eslint-plugin-wpvip/-/eslint-plugin-wpvip-0.11.0.tgz",
+      "integrity": "sha512-GfSGo2KbrRSPmmklL5YRiVONCFDQidF6agv7x9xU8UEmEw6jPNgndrD4yO7KCoEXX4OUYRDi9bZx1afky1TYng==",
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-        "@typescript-eslint/eslint-plugin": "6.13.1",
-        "@typescript-eslint/parser": "6.13.1",
+        "@babel/eslint-parser": "7.24.5",
+        "@rushstack/eslint-patch": "1.10.2",
+        "@typescript-eslint/eslint-plugin": "7.8.0",
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-        "eslint-plugin-import": "2.29.0",
-        "eslint-plugin-jest": "27.6.0",
+        "eslint-plugin-import": "2.29.1",
+        "eslint-plugin-jest": "28.5.0",
         "eslint-plugin-jsdoc": "46.8.2",
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@@ -222,12 +222,12 @@
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         "eslint-plugin-react-hooks": "4.6.0",
         "eslint-plugin-security": "1.7.1",
-        "eslint-plugin-unused-imports": "3.0.0",
+        "eslint-plugin-unused-imports": "3.2.0",
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         "globals": "13.23.0"
       },
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-        "eslint": ">=8"
+        "eslint": "^8.56.0"
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@@ -506,9 +506,9 @@
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         "graphemer": "^1.4.0",
-        "ignore": "^5.2.4",
+        "ignore": "^5.3.1",
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-        "semver": "^7.5.4",
-        "ts-api-utils": "^1.0.1"
+        "semver": "^7.6.0",
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+      "version": "3.2.0",
+      "resolved": "https://registry.npmjs.org/eslint-plugin-unused-imports/-/eslint-plugin-unused-imports-3.2.0.tgz",
+      "integrity": "sha512-6uXyn6xdINEpxE1MtDjxQsyXB37lfyO2yKGVVgtD7WEWQGORSOZjgrD6hBhvGv4/SO+TOlS+UnC6JppRqbuwGQ==",
       "dev": true,
       "requires": {
         "eslint-rule-composer": "^0.3.0"
@@ -19305,9 +19145,9 @@
       "integrity": "sha512-dcyqhDvX1C46lXZcVqCpK+FtMRQVdIMN6/Df5js2zouUsqG7I6sFxitIC+7KYK29KdXOLHdu9zL4sFnoVQnqaA=="
     },
     "ignore": {
-      "version": "5.2.4",
-      "resolved": "https://registry.npmjs.org/ignore/-/ignore-5.2.4.tgz",
-      "integrity": "sha512-MAb38BcSbH0eHNBxn7ql2NH/kX33OkB3lZ1BNdh7ENeRChHTYsTvWrMubiIAMNS2llXEEgZ1MUOBtXChP3kaFQ==",
+      "version": "5.3.1",
+      "resolved": "https://registry.npmjs.org/ignore/-/ignore-5.3.1.tgz",
+      "integrity": "sha512-5Fytz/IraMjqpwfd34ke28PTVMjZjJG2MPn5t7OE4eUCUNf8BAa7b5WUS9/Qvr6mwOQS7Mk6vdsMno5he+T8Xw==",
       "dev": true
     },
     "import-fresh": {
@@ -21850,9 +21690,9 @@
       "dev": true
     },
     "rimraf": {
-      "version": "5.0.5",
-      "resolved": "https://registry.npmjs.org/rimraf/-/rimraf-5.0.5.tgz",
-      "integrity": "sha512-CqDakW+hMe/Bz202FPEymy68P+G50RfMQK+Qo5YUqc9SPipvbGjCGKd0RSKEelbsfQuw3g5NZDSrlZZAJurH1A==",
+      "version": "5.0.7",
+      "resolved": "https://registry.npmjs.org/rimraf/-/rimraf-5.0.7.tgz",
+      "integrity": "sha512-nV6YcJo5wbLW77m+8KjH8aB/7/rxQy9SZ0HY5shnwULfS+9nmTtVXAJET5NdZmCzA4fPI/Hm1wo/Po/4mopOdg==",
       "dev": true,
       "requires": {
         "glob": "^10.3.7"
@@ -21954,22 +21794,9 @@
       "integrity": "sha512-NqVDv9TpANUjFm0N8uM5GxL36UgKi9/atZw+x7YFnQ8ckwFGKrl4xX4yWtrey3UJm5nP1kUbnYgLopqWNSRhWw=="
     },
     "semver": {
-      "version": "7.6.0",
-      "resolved": "https://registry.npmjs.org/semver/-/semver-7.6.0.tgz",
-      "integrity": "sha512-EnwXhrlwXMk9gKu5/flx5sv/an57AkRplG3hTK68W7FRDN+k+OWBj65M7719OkA82XLBxrcX0KSHj+X5COhOVg==",
-      "requires": {
-        "lru-cache": "^6.0.0"
-      },
-      "dependencies": {
-        "lru-cache": {
-          "version": "6.0.0",
-          "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-6.0.0.tgz",
-          "integrity": "sha512-Jo6dJ04CmSjuznwJSS3pUeWmd/H0ffTlkXXgwZi+eq1UCmqQwCh+eLsYOYCwY991i2Fah4h1BEMCx4qThGbsiA==",
-          "requires": {
-            "yallist": "^4.0.0"
-          }
-        }
-      }
+      "version": "7.6.2",
+      "resolved": "https://registry.npmjs.org/semver/-/semver-7.6.2.tgz",
+      "integrity": "sha512-FNAIBWCx9qcRhoHcgcJ0gvU7SN1lYU2ZXuSfl04bSC5OpvDHFyJCjdNHomPXxjQlCBU67YW64PzY7/VIEH7F2w=="
     },
     "semver-diff": {
       "version": "4.0.0",
@@ -22540,9 +22367,9 @@
       }
     },
     "ts-api-utils": {
-      "version": "1.0.3",
-      "resolved": "https://registry.npmjs.org/ts-api-utils/-/ts-api-utils-1.0.3.tgz",
-      "integrity": "sha512-wNMeqtMz5NtwpT/UZGY5alT+VoKdSsOOP/kqHFcUW1P/VRhH2wJ48+DN2WwUliNbQ976ETwDL0Ifd2VVvgonvg==",
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/ts-api-utils/-/ts-api-utils-1.3.0.tgz",
+      "integrity": "sha512-UQMIo7pb8WRomKR1/+MFVLTroIvDVtMX3K6OUir8ynLyzB8Jeriont2bTAtmNPa1ekAgN7YPDyf6V+ygrdU+eQ==",
       "dev": true,
       "requires": {}
     },
@@ -22557,9 +22384,9 @@
       }
     },
     "tsconfig-paths": {
-      "version": "3.14.2",
-      "resolved": "https://registry.npmjs.org/tsconfig-paths/-/tsconfig-paths-3.14.2.tgz",
-      "integrity": "sha512-o/9iXgCYc5L/JxCHPe3Hvh8Q/2xm5Z+p18PESBU6Ff33695QnCHBEjcytY2q19ua7Mbl/DavtBOLq+oG0RCL+g==",
+      "version": "3.15.0",
+      "resolved": "https://registry.npmjs.org/tsconfig-paths/-/tsconfig-paths-3.15.0.tgz",
+      "integrity": "sha512-2Ac2RgzDe/cn48GvOe3M+o82pEFewD3UPbyoUHHdKasHwJKjds4fLXWf/Ux5kATBKN20oaFGu+jbElp1pos0mg==",
       "dev": true,
       "requires": {
         "@types/json5": "^0.0.29",
@@ -22584,15 +22411,6 @@
       "resolved": "https://registry.npmjs.org/tslib/-/tslib-1.14.1.tgz",
       "integrity": "sha512-Xni35NKzjgMrwevysHTCArtLDpPvye8zV/0E4EyYn43P7/7qvQwPh9BGkHewbMulVntbigmcT7rdX3BNo9wRJg=="
     },
-    "tsutils": {
-      "version": "3.21.0",
-      "resolved": "https://registry.npmjs.org/tsutils/-/tsutils-3.21.0.tgz",
-      "integrity": "sha512-mHKK3iUXL+3UF6xL5k0PEhKRUBKPBCv/+RkEOpjRWxxx27KKRBmmA60A9pgOUvMi8GKhRMPEmjBRPzs2W7O1OA==",
-      "dev": true,
-      "requires": {
-        "tslib": "^1.8.1"
-      }
-    },
     "tunnel-agent": {
       "version": "0.6.0",
       "resolved": "https://registry.npmjs.org/tunnel-agent/-/tunnel-agent-0.6.0.tgz",
diff --git a/package.json b/package.json
index 8cd0410da9..569134a266 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@automattic/vip",
-  "version": "2.39.7-dev.0",
+  "version": "2.39.8-dev.0",
   "description": "The VIP Javascript library & CLI",
   "main": "index.js",
   "bin": {
@@ -106,7 +106,7 @@
   },
   "homepage": "https://github.com/Automattic/vip#readme",
   "devDependencies": {
-    "@automattic/eslint-plugin-wpvip": "0.9.1",
+    "@automattic/eslint-plugin-wpvip": "0.11.0",
     "@babel/cli": "7.24.5",
     "@babel/core": "7.24.5",
     "@babel/preset-env": "7.24.5",
@@ -135,7 +135,7 @@
     "jest": "^29.7.0",
     "nock": "13.5.4",
     "prettier": "npm:wp-prettier@2.8.5",
-    "rimraf": "5.0.5",
+    "rimraf": "5.0.7",
     "typescript": "^5.2.2"
   },
   "dependencies": {
@@ -164,7 +164,7 @@
     "node-fetch": "^2.6.1",
     "open": "^10.0.0",
     "proxy-from-env": "^1.1.0",
-    "semver": "7.6.0",
+    "semver": "7.6.2",
     "shelljs": "^0.8.5",
     "single-line-log": "1.1.2",
     "socket.io-client": "^4.5.3",
diff --git a/src/bin/vip-dev-env-info.js b/src/bin/vip-dev-env-info.js
index 58edf3953b..fbd74c1e21 100755
--- a/src/bin/vip-dev-env-info.js
+++ b/src/bin/vip-dev-env-info.js
@@ -37,12 +37,19 @@ command()
 	.option( 'extended', 'Show extended information about the dev environment' )
 	.examples( examples )
 	.argv( process.argv, async ( arg, opt ) => {
-		const slug = await getEnvironmentName( opt );
-
+		let trackingInfo;
+		let slug;
 		const lando = await bootstrapLando();
-		await validateDependencies( lando, slug );
 
-		const trackingInfo = opt.all ? { all: true } : getEnvTrackingInfo( slug );
+		if ( opt.all ) {
+			trackingInfo = { all: true };
+			slug = '';
+		} else {
+			slug = await getEnvironmentName( opt );
+			trackingInfo = getEnvTrackingInfo( slug );
+		}
+
+		await validateDependencies( lando, slug );
 		await trackEvent( 'dev_env_info_command_execute', trackingInfo );
 
 		debug( 'Args: ', arg, 'Options: ', opt );
diff --git a/src/bin/vip-dev-env-start.js b/src/bin/vip-dev-env-start.js
index 94da10981a..3ed12493cc 100755
--- a/src/bin/vip-dev-env-start.js
+++ b/src/bin/vip-dev-env-start.js
@@ -46,8 +46,12 @@ command()
 
 		const startProcessing = new Date();
 
+		const versions = await lando.engine.daemon.getVersions();
 		const trackingInfo = getEnvTrackingInfo( slug );
 		trackingInfo.vscode = Boolean( opt.vscode );
+		trackingInfo.docker = versions.engine;
+		trackingInfo.docker_compose = versions.compose;
+
 		await trackEvent( 'dev_env_start_command_execute', trackingInfo );
 
 		debug( 'Args: ', arg, 'Options: ', opt );
diff --git a/src/lib/dev-environment/dev-environment-cli.ts b/src/lib/dev-environment/dev-environment-cli.ts
index ea8393f7ca..4dab86e875 100644
--- a/src/lib/dev-environment/dev-environment-cli.ts
+++ b/src/lib/dev-environment/dev-environment-cli.ts
@@ -611,7 +611,8 @@ export function promptForBoolean( message: string, initial: boolean ): Promise<
 	if ( isStdinTTY ) {
 		const confirm = new Confirm( {
 			message,
-			initial: initial.toString(),
+			// eslint-disable-next-line @typescript-eslint/no-explicit-any,@typescript-eslint/no-unsafe-assignment
+			initial: initial as any, // TS definition is wrong, so we need to bypass it to show the correct hint.
 		} );
 
 		return confirm.run();
diff --git a/src/lib/dev-environment/dev-environment-lando.ts b/src/lib/dev-environment/dev-environment-lando.ts
index 5d9ac775ce..c144124d0c 100644
--- a/src/lib/dev-environment/dev-environment-lando.ts
+++ b/src/lib/dev-environment/dev-environment-lando.ts
@@ -8,7 +8,7 @@ import landoBuildTask from 'lando/plugins/lando-tooling/lib/build';
 import { lookup } from 'node:dns/promises';
 import { mkdir, rename } from 'node:fs/promises';
 import { tmpdir } from 'node:os';
-import path from 'node:path';
+import path, { dirname } from 'node:path';
 import xdgBasedir from 'xdg-basedir';
 
 import {
@@ -33,9 +33,10 @@ const debug = debugLib( DEBUG_KEY );
  * @return {Promise<LandoConfig>} Lando configuration
  */
 async function getLandoConfig(): Promise< LandoConfig > {
-	const nodeModulesPath = path.join( __dirname, '..', '..', '..', 'node_modules' );
-	const landoPath = path.join( nodeModulesPath, 'lando' );
-	const atLandoPath = path.join( nodeModulesPath, '@lando' );
+	// 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' ) ) );
+	// The path will be smth like `yarn/global/node_modules/@lando/compose/index.js`; we need the path up to `@lando` (inclusive)
+	const atLandoPath = dirname( dirname( require.resolve( '@lando/compose' ) ) );
 
 	debug( `Getting Lando config, using paths '${ landoPath }' and '${ atLandoPath }' for plugins` );