diff --git a/__tests__/lib/dev-environment/dev-environment-core.js b/__tests__/lib/dev-environment/dev-environment-core.js
index 99c668212..02b2e15f0 100644
--- a/__tests__/lib/dev-environment/dev-environment-core.js
+++ b/__tests__/lib/dev-environment/dev-environment-core.js
@@ -16,12 +16,21 @@ import {
 	resolveImportPath,
 	readEnvironmentData,
 } from '../../../src/lib/dev-environment/dev-environment-core';
+import {
+	isEnvUp,
+	landoInfo,
+	landoRebuild,
+	landoStart,
+	getProxyContainer,
+} from '../../../src/lib/dev-environment/dev-environment-lando';
 import { searchAndReplace } from '../../../src/lib/search-and-replace';
+import UserError from '../../../src/lib/user-error';
 import { xdgData } from '../../../src/lib/xdg-data';
 
 jest.mock( '../../../src/lib/api/app' );
 jest.mock( '../../../src/lib/search-and-replace' );
 jest.mock( '../../../src/lib/dev-environment/dev-environment-cli' );
+jest.mock( '../../../src/lib/dev-environment/dev-environment-lando' );
 
 describe( 'lib/dev-environment/dev-environment-core', () => {
 	const cleanup = () =>
@@ -65,6 +74,115 @@ describe( 'lib/dev-environment/dev-environment-core', () => {
 
 			return expect( promise ).rejects.toEqual( new Error( DEV_ENVIRONMENT_NOT_FOUND ) );
 		} );
+
+		describe( 'readiness polling and retry', () => {
+			const slug = 'readiness-test-slug';
+			const instanceData = JSON.stringify( {
+				siteSlug: slug,
+				wpTitle: 'Test',
+				multisite: false,
+				wordpress: { mode: 'image', tag: 'trunk' },
+				muPlugins: { mode: 'image' },
+				appCode: { mode: 'image' },
+				mediaRedirectDomain: '',
+				phpmyadmin: false,
+				xdebug: false,
+				php: 'php:8.2',
+				mailpit: false,
+				photon: false,
+				cron: false,
+				version: '2.3.2',
+			} );
+
+			beforeEach( () => {
+				const expectedPath = getEnvironmentPath( slug );
+				const instanceDataPath = path.join( expectedPath, 'instance_data.json' );
+				const _originalExistsSync = fs.existsSync;
+				const _originalReadFileSync = fs.readFileSync;
+				jest.spyOn( fs, 'existsSync' ).mockImplementation( fpath => {
+					if ( fpath === expectedPath ) {
+						return true;
+					}
+					return _originalExistsSync( fpath );
+				} );
+				jest.spyOn( fs, 'appendFileSync' ).mockReturnValue( undefined );
+				jest.spyOn( fs, 'readFileSync' ).mockImplementation( ( filePath, ...args ) => {
+					if ( filePath === instanceDataPath ) {
+						return instanceData;
+					}
+					return _originalReadFileSync( filePath, ...args );
+				} );
+				jest.spyOn( fs.promises, 'stat' ).mockResolvedValue( { isFile: () => true } );
+
+				getProxyContainer.mockResolvedValue( { State: { Running: true } } );
+				landoRebuild.mockResolvedValue( undefined );
+				landoStart.mockResolvedValue( undefined );
+				landoInfo.mockResolvedValue( {} );
+			} );
+
+			it( 'should succeed without retrying when environment is up on the first readiness check', async () => {
+				isEnvUp.mockResolvedValue( true );
+
+				await startEnvironment( {}, slug, {
+					skipRebuild: false,
+					skipWpVersionsCheck: true,
+				} );
+
+				expect( isEnvUp ).toHaveBeenCalledTimes( 1 );
+				expect( landoRebuild ).toHaveBeenCalledTimes( 1 );
+				expect( landoStart ).not.toHaveBeenCalled();
+			} );
+
+			it( 'should call landoStart retry when first readiness pass times out and succeed on second pass', async () => {
+				// First waitForEnvironmentToBeUp: all 6 attempts return false
+				// Second waitForEnvironmentToBeUp: succeeds on the first attempt
+				isEnvUp
+					.mockResolvedValueOnce( false )
+					.mockResolvedValueOnce( false )
+					.mockResolvedValueOnce( false )
+					.mockResolvedValueOnce( false )
+					.mockResolvedValueOnce( false )
+					.mockResolvedValueOnce( false )
+					.mockResolvedValueOnce( true );
+
+				jest.useFakeTimers();
+				try {
+					const promise = startEnvironment( {}, slug, {
+						skipRebuild: false,
+						skipWpVersionsCheck: true,
+					} );
+					await jest.runAllTimersAsync();
+					await promise;
+				} finally {
+					jest.useRealTimers();
+				}
+
+				expect( landoRebuild ).toHaveBeenCalledTimes( 1 );
+				expect( landoStart ).toHaveBeenCalledTimes( 1 ); // retry pass
+				expect( isEnvUp ).toHaveBeenCalledTimes( 7 ); // 6 failed + 1 success
+			} );
+
+			it( 'should throw UserError when environment never reaches a running state', async () => {
+				isEnvUp.mockResolvedValue( false ); // all attempts fail
+
+				jest.useFakeTimers();
+				try {
+					const promise = startEnvironment( {}, slug, {
+						skipRebuild: false,
+						skipWpVersionsCheck: true,
+					} );
+					// Register rejection handler before timers to prevent unhandled rejection
+					const assertion = expect( promise ).rejects.toThrow( UserError );
+					await jest.runAllTimersAsync();
+					await assertion;
+				} finally {
+					jest.useRealTimers();
+				}
+
+				expect( landoStart ).toHaveBeenCalledTimes( 1 ); // retry pass attempted
+				expect( isEnvUp ).toHaveBeenCalledTimes( 12 ); // 6 + 6 attempts
+			} );
+		} );
 	} );
 	describe( 'destroyEnvironment', () => {
 		it( 'should throw for NON existing folder', async () => {
diff --git a/npm-shrinkwrap.json b/npm-shrinkwrap.json
index 95238e011..cf287f0ba 100644
--- a/npm-shrinkwrap.json
+++ b/npm-shrinkwrap.json
@@ -303,6 +303,7 @@
       "integrity": "sha512-CGOfOJqWjg2qW/Mb6zNsDm+u5vFQ8DxXfbM09z69p5Z6+mE1ikP2jUXw+j42Pf1XTYED2Rni5f95npYeuwMDQA==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@babel/code-frame": "^7.29.0",
         "@babel/generator": "^7.29.0",
@@ -2271,7 +2272,6 @@
       "integrity": "sha512-aw1gNayWpdI/jSYVgzN5pL0cfzU02GT3NBpeT/DXbx1/1x7ZKxFPd9bwrzygx/qiwIQiJ1sw/zD8qY/kRvlGHA==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "dependencies": {
         "@eslint/object-schema": "^2.1.7",
         "debug": "^4.3.1",
@@ -2287,7 +2287,6 @@
       "integrity": "sha512-9T9UjW3r0UW5c1Q7GTwllptXwhvYmEzFhzMfZ9H7FQWt+uZePjZPjBP/W1ZEyZ1twGWom5/56TF4lPcqjnDHcg==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "balanced-match": "^1.0.0",
         "concat-map": "0.0.1"
@@ -2299,7 +2298,6 @@
       "integrity": "sha512-J7p63hRiAjw1NDEww1W7i37+ByIrOWO5XQQAzZ3VOcL0PNybwpfmV/N05zFAzwQ9USyEcX6t3UO+K5aqBQOIHw==",
       "dev": true,
       "license": "ISC",
-      "peer": true,
       "dependencies": {
         "brace-expansion": "^1.1.7"
       },
@@ -2313,7 +2311,6 @@
       "integrity": "sha512-gBrxN88gOIf3R7ja5K9slwNayVcZgK6SOUORm2uBzTeIEfeVaIhOpCtTox3P6R7o2jLFwLFTLnC7kU/RGcYEgw==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "dependencies": {
         "@eslint/core": "^0.17.0"
       },
@@ -2327,7 +2324,6 @@
       "integrity": "sha512-yL/sLrpmtDaFEiUj1osRP4TI2MDz1AddJL+jZ7KSqvBuliN4xqYY54IfdN8qD8Toa6g1iloph1fxQNkjOxrrpQ==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "dependencies": {
         "@types/json-schema": "^7.0.15"
       },
@@ -2341,7 +2337,6 @@
       "integrity": "sha512-Kr+LPIUVKz2qkx1HAMH8q1q6azbqBAsXJUxBl/ODDuVPX45Z9DfwB8tPjTi6nNZ8BuM3nbJxC5zCAg5elnBUTQ==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "ajv": "^6.12.4",
         "debug": "^4.3.2",
@@ -2366,7 +2361,6 @@
       "integrity": "sha512-9T9UjW3r0UW5c1Q7GTwllptXwhvYmEzFhzMfZ9H7FQWt+uZePjZPjBP/W1ZEyZ1twGWom5/56TF4lPcqjnDHcg==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "balanced-match": "^1.0.0",
         "concat-map": "0.0.1"
@@ -2378,7 +2372,6 @@
       "integrity": "sha512-oahGvuMGQlPw/ivIYBjVSrWAfWLBeku5tpPE2fOPLi+WHffIWbuh2tCjhyQhTBPMf5E9jDEH4FOmTYgYwbKwtQ==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=18"
       },
@@ -2392,7 +2385,6 @@
       "integrity": "sha512-J7p63hRiAjw1NDEww1W7i37+ByIrOWO5XQQAzZ3VOcL0PNybwpfmV/N05zFAzwQ9USyEcX6t3UO+K5aqBQOIHw==",
       "dev": true,
       "license": "ISC",
-      "peer": true,
       "dependencies": {
         "brace-expansion": "^1.1.7"
       },
@@ -2406,7 +2398,6 @@
       "integrity": "sha512-q1mjIoW1VX4IvSocvM/vbTiveKC4k9eLrajNEuSsmjymSDEbpGddtpfOoN7YGAqBK3NG+uqo8ia4PDTt8buCYA==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": "^18.18.0 || ^20.9.0 || >=21.1.0"
       },
@@ -2420,7 +2411,6 @@
       "integrity": "sha512-VtAOaymWVfZcmZbp6E2mympDIHvyjXs/12LqWYjVw6qjrfF+VK+fyG33kChz3nnK+SU5/NeHOqrTEHS8sXO3OA==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "engines": {
         "node": "^18.18.0 || ^20.9.0 || >=21.1.0"
       }
@@ -2431,7 +2421,6 @@
       "integrity": "sha512-43/qtrDUokr7LJqoF2c3+RInu/t4zfrpYdoSDfYyhg52rwLV6TnOvdG4fXm7IkSB3wErkcmJS9iEhjVtOSEjjA==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "dependencies": {
         "@eslint/core": "^0.17.0",
         "levn": "^0.4.1"
@@ -2504,7 +2493,6 @@
       "integrity": "sha512-5DyQ4+1JEUzejeK1JGICcideyfUbGixgS9jNgex5nqkW+cY7WZhxBigmieN5Qnw9ZosSNVC9KQKyb+GUaGyKUA==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "engines": {
         "node": ">=18.18.0"
       }
@@ -2515,7 +2503,6 @@
       "integrity": "sha512-/zUx+yOsIrG4Y43Eh2peDeKCxlRt/gET6aHfaKpuq267qXdYDFViVHfMaLyygZOnl0kGWxFIgsBy8QFuTLUXEQ==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "dependencies": {
         "@humanfs/core": "^0.19.1",
         "@humanwhocodes/retry": "^0.4.0"
@@ -2530,7 +2517,6 @@
       "integrity": "sha512-bxveV4V8v5Yb4ncFTT3rPSgZBOpCkjfK0y4oVVVJwIuDVBRMDXrPyXRL988i5ap9m9bnyEEjWfm5WkBmtffLfA==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "engines": {
         "node": ">=12.22"
       },
@@ -2545,7 +2531,6 @@
       "integrity": "sha512-bV0Tgo9K4hfPCek+aMAn81RppFKv2ySDQeMoSZuvTASywNTnVJCArCZE2FWqpvIatKu7VMRLWlR1EazvVhDyhQ==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "engines": {
         "node": ">=18.18"
       },
@@ -4071,8 +4056,7 @@
       "resolved": "https://registry.npmjs.org/@types/json-schema/-/json-schema-7.0.15.tgz",
       "integrity": "sha512-5+fP8P8MFNC+AyZCDxrB2pkZFPGzqQWUzpSeuuVLvm8VMcorNYavBqoFcxK8bQz4Qsbn4oUEEem4wDLfcysGHA==",
       "dev": true,
-      "license": "MIT",
-      "peer": true
+      "license": "MIT"
     },
     "node_modules/@types/json5": {
       "version": "0.0.29",
@@ -4988,6 +4972,7 @@
       "integrity": "sha512-NZyJarBfL7nWwIq+FDL6Zp/yHEhePMNnnJ0y3qfieCrmNvYct8uvtiV41UvlSe6apAfk0fY1FbWx+NwfmpvtTg==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "bin": {
         "acorn": "bin/acorn"
       },
@@ -5020,7 +5005,6 @@
       "integrity": "sha512-j3fVLgvTo527anyYyJOGTYJbG+vnnQYvE0m5mmkc1TK+nxAppkCLMIL0aZ4dblVCNoGShhm+kzE4ZUykBoMg4g==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "fast-deep-equal": "^3.1.1",
         "fast-json-stable-stringify": "^2.0.0",
@@ -5817,6 +5801,7 @@
         }
       ],
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "baseline-browser-mapping": "^2.9.0",
         "caniuse-lite": "^1.0.30001759",
@@ -6439,6 +6424,7 @@
       "resolved": "https://registry.npmjs.org/debug/-/debug-4.4.3.tgz",
       "integrity": "sha512-RGwwWnwQvkVfavKVt22FGLw+xYSdzARwm0ru6DhTVA3umU5hZc28V3kO4stgYryrTlLpuvgI9GiijltAjNbcqA==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "ms": "^2.1.3"
       },
@@ -6496,8 +6482,7 @@
       "resolved": "https://registry.npmjs.org/deep-is/-/deep-is-0.1.4.tgz",
       "integrity": "sha512-oIPzksmTg4/MriiaYGO+okXDT7ztn/w3Eptv/+gSIdMdKsJo0u4CfYNFJPy+4SKMuCqGw2wxnA+URMg3t8a/bQ==",
       "dev": true,
-      "license": "MIT",
-      "peer": true
+      "license": "MIT"
     },
     "node_modules/deepmerge": {
       "version": "4.3.1",
@@ -7104,6 +7089,7 @@
       "integrity": "sha512-82GZUjRS0p/jganf6q1rEO25VSoHH0hKPCTrgillPjdI/3bgBhAE1QzHrHTizjpRvy6pGAvKjDJtk2pF9NDq8w==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "bin": {
         "eslint-config-prettier": "bin/cli.js"
       },
@@ -7230,6 +7216,7 @@
       "integrity": "sha512-whOE1HFo/qJDyX4SnXzP4N6zOWn79WhnCUY/iDR0mPfQZO8wcYE4JClzI2oZrhBnnMUCBCHZhO6VQyoBU95mZA==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@rtsao/scc": "^1.1.0",
         "array-includes": "^3.1.9",
@@ -7652,7 +7639,6 @@
       "integrity": "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "color-convert": "^2.0.1"
       },
@@ -7669,7 +7655,6 @@
       "integrity": "sha512-9T9UjW3r0UW5c1Q7GTwllptXwhvYmEzFhzMfZ9H7FQWt+uZePjZPjBP/W1ZEyZ1twGWom5/56TF4lPcqjnDHcg==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "balanced-match": "^1.0.0",
         "concat-map": "0.0.1"
@@ -7681,7 +7666,6 @@
       "integrity": "sha512-oKnbhFyRIXpUuez8iBMmyEa4nbj4IOQyuhc/wy9kY7/WVPcwIO9VA668Pu8RkO7+0G76SLROeyw9CpQ061i4mA==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "ansi-styles": "^4.1.0",
         "supports-color": "^7.1.0"
@@ -7699,7 +7683,6 @@
       "integrity": "sha512-RRECPsj7iu/xb5oKYcsFHSppFNnsj/52OVTRKb4zP5onXwVF3zVmmToNcOfGC+CRDpfK/U584fMg38ZHCaElKQ==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "color-name": "~1.1.4"
       },
@@ -7712,8 +7695,7 @@
       "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.4.tgz",
       "integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==",
       "dev": true,
-      "license": "MIT",
-      "peer": true
+      "license": "MIT"
     },
     "node_modules/eslint/node_modules/eslint-scope": {
       "version": "8.4.0",
@@ -7721,7 +7703,6 @@
       "integrity": "sha512-sNXOfKCn74rt8RICKMvJS7XKV/Xk9kA7DyJr8mJik3S7Cwgy3qlkkmyS2uQB3jiJg6VNdZd/pDBJu0nvG2NlTg==",
       "dev": true,
       "license": "BSD-2-Clause",
-      "peer": true,
       "dependencies": {
         "esrecurse": "^4.3.0",
         "estraverse": "^5.2.0"
@@ -7739,7 +7720,6 @@
       "integrity": "sha512-Uhdk5sfqcee/9H/rCOJikYz67o0a2Tw2hGRPOG2Y1R2dg7brRe1uG0yaNQDHu+TO/uQPF/5eCapvYSmHUjt7JQ==",
       "dev": true,
       "license": "Apache-2.0",
-      "peer": true,
       "engines": {
         "node": "^18.18.0 || ^20.9.0 || >=21.1.0"
       },
@@ -7753,7 +7733,6 @@
       "integrity": "sha512-XxwI8EOhVQgWp6iDL+3b0r86f4d6AX6zSU55HfB4ydCEuXLXc5FcYeOu+nnGftS4TEju/11rt4KJPTMgbfmv4A==",
       "dev": true,
       "license": "ISC",
-      "peer": true,
       "dependencies": {
         "is-glob": "^4.0.3"
       },
@@ -7767,7 +7746,6 @@
       "integrity": "sha512-J7p63hRiAjw1NDEww1W7i37+ByIrOWO5XQQAzZ3VOcL0PNybwpfmV/N05zFAzwQ9USyEcX6t3UO+K5aqBQOIHw==",
       "dev": true,
       "license": "ISC",
-      "peer": true,
       "dependencies": {
         "brace-expansion": "^1.1.7"
       },
@@ -7932,8 +7910,7 @@
       "resolved": "https://registry.npmjs.org/fast-deep-equal/-/fast-deep-equal-3.1.3.tgz",
       "integrity": "sha512-f3qQ9oQy9j2AhBe/H9VC91wLmKBCCU/gDOnKNAYG5hswO7BLKj09Hc5HYNz9cGI++xlpDCIgDaitVs03ATR84Q==",
       "dev": true,
-      "license": "MIT",
-      "peer": true
+      "license": "MIT"
     },
     "node_modules/fast-diff": {
       "version": "1.3.0",
@@ -7970,8 +7947,7 @@
       "resolved": "https://registry.npmjs.org/fast-levenshtein/-/fast-levenshtein-2.0.6.tgz",
       "integrity": "sha512-DCXu6Ifhqcks7TZKY3Hxp3y6qphY5SJZmrWMDrKcERSOXWQdMhU9Ig/PYrzyw/ul9jOIyh0N4M0tbC5hodg8dw==",
       "dev": true,
-      "license": "MIT",
-      "peer": true
+      "license": "MIT"
     },
     "node_modules/fastq": {
       "version": "1.19.1",
@@ -8033,7 +8009,6 @@
       "integrity": "sha512-XXTUwCvisa5oacNGRP9SfNtYBNAMi+RPwBFmblZEF7N7swHYQS6/Zfk7SRwx4D5j3CH211YNRco1DEMNVfZCnQ==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "flat-cache": "^4.0.0"
       },
@@ -8087,7 +8062,6 @@
       "integrity": "sha512-78/PXT1wlLLDgTzDs7sjq9hzz0vXD+zn+7wypEe4fXQxCmdmqfGsEPQxmiCSQI3ajFV91bVSsvNtrJRiW6nGng==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "locate-path": "^6.0.0",
         "path-exists": "^4.0.0"
@@ -8105,7 +8079,6 @@
       "integrity": "sha512-f7ccFPK3SXFHpx15UIGyRJ/FJQctuKZ0zVuN3frBo4HnK3cay9VEW0R6yPYFHC0AgqhukPzKjq22t5DmAyqGyw==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "flatted": "^3.2.9",
         "keyv": "^4.5.4"
@@ -8119,8 +8092,7 @@
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