diff --git a/.changeset/metal-pillows-report.md b/.changeset/metal-pillows-report.md
new file mode 100644
index 0000000000..4e217cb085
--- /dev/null
+++ b/.changeset/metal-pillows-report.md
@@ -0,0 +1,5 @@
+---
+"stylelint": patch
+---
+
+Fixed: false negatives on second run for cache and `severity` option
diff --git a/lib/__tests__/standalone-cache.test.js b/lib/__tests__/standalone-cache.test.js
index 45c629041c..7766a5f610 100644
--- a/lib/__tests__/standalone-cache.test.js
+++ b/lib/__tests__/standalone-cache.test.js
@@ -119,6 +119,30 @@ describe('standalone cache', () => {
 		expect(cache.getKey(newFileDest)).toBeUndefined();
 	});
 
+	it('warning files are not cached', async () => {
+		await fs.copyFile(invalidFile, newFileDest);
+
+		const { errored, results } = await standalone(
+			getConfig({
+				config: {
+					rules: { 'block-no-empty': [true, { severity: 'warning' }] },
+				},
+			}),
+		);
+
+		expect(errored).toBe(false);
+
+		// cache is discarded because config changed
+		expect(results.some((file) => isChanged(file, validFile))).toBe(true);
+		expect(results.some((file) => isChanged(file, newFileDest))).toBe(true);
+
+		const { cache } = fCache.createFromFile(expectedCacheFilePath);
+
+		expect(typeof cache.getKey(validFile)).toBe('object');
+		expect(cache.getKey(validFile)).toBeTruthy();
+		expect(cache.getKey(newFileDest)).toBeUndefined();
+	});
+
 	it('files with syntax errors are not cached', async () => {
 		await fs.copyFile(syntaxErrorFile, newFileDest);
 
diff --git a/lib/lintPostcssResult.js b/lib/lintPostcssResult.js
index 23d0f75e5f..0cde1a0af9 100644
--- a/lib/lintPostcssResult.js
+++ b/lib/lintPostcssResult.js
@@ -20,6 +20,7 @@ function lintPostcssResult(stylelintOptions, postcssResult, config) {
 	postcssResult.stylelint.customMessages = {};
 	postcssResult.stylelint.ruleMetadata = {};
 	postcssResult.stylelint.stylelintError = false;
+	postcssResult.stylelint.stylelintWarning = false;
 	postcssResult.stylelint.quiet = config.quiet;
 	postcssResult.stylelint.config = config;
 
diff --git a/lib/lintSource.js b/lib/lintSource.js
index bd101d4a61..01029a2070 100644
--- a/lib/lintSource.js
+++ b/lib/lintSource.js
@@ -116,6 +116,7 @@ function createEmptyStylelintPostcssResult() {
 		disabledRanges: {},
 		ignored: true,
 		stylelintError: false,
+		stylelintWarning: false,
 	};
 }
 
diff --git a/lib/standalone.js b/lib/standalone.js
index b74659ab7d..5f2781ab91 100644
--- a/lib/standalone.js
+++ b/lib/standalone.js
@@ -216,7 +216,10 @@ async function standalone({
 					cache: useCache,
 				});
 
-				if (postcssResult.stylelint.stylelintError && useCache) {
+				if (
+					(postcssResult.stylelint.stylelintError || postcssResult.stylelint.stylelintWarning) &&
+					useCache
+				) {
 					debug(`${absoluteFilepath} contains linting errors and will not be cached.`);
 					stylelint._fileCache.removeEntry(absoluteFilepath);
 				}
diff --git a/lib/utils/report.js b/lib/utils/report.js
index a84ae5e808..befcd739c5 100644
--- a/lib/utils/report.js
+++ b/lib/utils/report.js
@@ -78,6 +78,10 @@ module.exports = function report(problem) {
 		result.stylelint.stylelintError = true;
 	}
 
+	if (!result.stylelint.stylelintWarning && severity === 'warning') {
+		result.stylelint.stylelintWarning = true;
+	}
+
 	/** @type {import('stylelint').WarningOptions} */
 	const warningProperties = {
 		severity,
diff --git a/types/stylelint/index.d.ts b/types/stylelint/index.d.ts
index 1a12c44f81..bb1c7681ab 100644
--- a/types/stylelint/index.d.ts
+++ b/types/stylelint/index.d.ts
@@ -104,6 +104,7 @@ declare module 'stylelint' {
 			disabledWarnings?: DisabledWarning[];
 			ignored?: boolean;
 			stylelintError?: boolean;
+			stylelintWarning?: boolean;
 			disableWritingFix?: boolean;
 			config?: Config;
 			ruleDisableFix?: boolean;