diff --git a/src/analyze/core-js.ts b/src/analyze/core-js.ts
index 06831fa..d2a072a 100644
--- a/src/analyze/core-js.ts
+++ b/src/analyze/core-js.ts
@@ -65,7 +65,8 @@ export async function runCoreJsAnalysis(
         messages.push({
           severity: 'warning',
           score: 0,
-          message: `Broad core-js import "${specifier}" in ${filePath} loads all polyfills at once. Import only the specific modules you need.`
+          file: filePath,
+          message: `Broad core-js import "${specifier}" loads all polyfills at once. Import only the specific modules you need.`
         });
       } else if (specifier.startsWith('core-js/modules/')) {
         const moduleName = specifier.slice('core-js/modules/'.length);
@@ -73,7 +74,8 @@ export async function runCoreJsAnalysis(
           messages.push({
             severity: 'suggestion',
             score: 0,
-            message: `core-js polyfill "${moduleName}" imported in ${filePath} is unnecessary - your target engines already support this natively.`
+            file: filePath,
+            message: `core-js polyfill "${moduleName}" is unnecessary - your target engines already support this natively.`
           });
         }
       }
diff --git a/src/analyze/publint.ts b/src/analyze/publint.ts
index 5425b4f..c1b722f 100644
--- a/src/analyze/publint.ts
+++ b/src/analyze/publint.ts
@@ -15,6 +15,7 @@ export async function runPublint(
       result.messages.push({
         severity: problem.type,
         score: 0,
+        file: 'package.json',
         message: formatMessage(problem, publintResult.pkg) ?? ''
       });
     }
diff --git a/src/analyze/replacements.ts b/src/analyze/replacements.ts
index 36916af..9ad7960 100644
--- a/src/analyze/replacements.ts
+++ b/src/analyze/replacements.ts
@@ -175,6 +175,7 @@ export async function runReplacements(
     result.messages.push({
       severity: 'warning',
       score: 0,
+      file: 'package.json',
       message,
       ...(fixableBy && {fixableBy})
     });
diff --git a/src/analyze/web-features-codemods.ts b/src/analyze/web-features-codemods.ts
index c0c8ae3..39a1be3 100644
--- a/src/analyze/web-features-codemods.ts
+++ b/src/analyze/web-features-codemods.ts
@@ -60,7 +60,8 @@ export async function runWebFeaturesCodemodsAnalysis(
       messages.push({
         severity: 'suggestion',
         score: 0,
-        message: `File "${filePath}" can use newer web features: ${matches.join(', ')}.`
+        file: filePath,
+        message: `Can use newer web features: ${matches.join(', ')}.`
       });
     }
   }
diff --git a/src/commands/analyze.ts b/src/commands/analyze.ts
index 09ad0f5..cdcf8ad 100644
--- a/src/commands/analyze.ts
+++ b/src/commands/analyze.ts
@@ -197,11 +197,31 @@ export async function run(ctx: CommandContext<typeof meta>) {
     const width = process.stdout?.columns ?? 80;
     const maxContentWidth = Math.max(20, width - 4);
 
-    const formatBulletMessage = (text: string, bullet: string) =>
-      wrapAnsi(text, maxContentWidth)
+    const labels = {
+      error: {text: 'error', color: 'red'},
+      warning: {text: 'warning', color: 'yellow'},
+      suggestion: {text: 'suggestion', color: 'blue'}
+    } as const;
+
+    const labelWidth = Math.max(
+      ...Object.values(labels).map((l) => l.text.length)
+    );
+    // Two leading spaces, then the severity column, then two spaces before text.
+    const gutter = 2 + labelWidth + 2;
+
+    const formatBulletMessage = (
+      text: string,
+      label: (typeof labels)[keyof typeof labels]
+    ) => {
+      const severity = styleText(label.color, label.text.padEnd(labelWidth));
+      const indent = ' '.repeat(gutter);
+      return wrapAnsi(text, maxContentWidth)
         .split('\n')
-        .map((line, i) => (i === 0 ? `  ${bullet} ${line}` : `    ${line}`))
+        .map((line, i) =>
+          i === 0 ? `  ${severity}  ${line}` : `${indent}${line}`
+        )
         .join('\n');
+    };
 
     const errorMessages = visibleMessages.filter((m) => m.severity === 'error');
     const warningMessages = visibleMessages.filter(
@@ -211,38 +231,35 @@ export async function run(ctx: CommandContext<typeof meta>) {
       (m) => m.severity === 'suggestion'
     );
 
-    // Display errors
-    if (errorMessages.length > 0) {
-      prompts.log.message(styleText('red', 'Errors:'), {spacing: 0});
-      for (const msg of errorMessages) {
-        const bullet = styleText('red', '•');
-        prompts.log.message(formatBulletMessage(msg.message, bullet), {
-          spacing: 0
-        });
-      }
-      prompts.log.message('', {spacing: 0});
-    }
-
-    // Display warnings
-    if (warningMessages.length > 0) {
-      prompts.log.message(styleText('yellow', 'Warnings:'), {spacing: 0});
-      for (const msg of warningMessages) {
-        const bullet = styleText('yellow', '•');
-        prompts.log.message(formatBulletMessage(msg.message, bullet), {
-          spacing: 0
-        });
+    const groups = new Map<string | undefined, Message[]>();
+    for (const msg of visibleMessages) {
+      const existing = groups.get(msg.file);
+      if (existing) {
+        existing.push(msg);
+      } else {
+        groups.set(msg.file, [msg]);
       }
-      prompts.log.message('', {spacing: 0});
     }
-
-    // Display suggestions
-    if (suggestionMessages.length > 0) {
-      prompts.log.message(styleText('blue', 'Suggestions:'), {spacing: 0});
-      for (const msg of suggestionMessages) {
-        const bullet = styleText('blue', '•');
-        prompts.log.message(formatBulletMessage(msg.message, bullet), {
-          spacing: 0
-        });
+    const sortedGroups = [...groups.entries()].sort(([a], [b]) => {
+      if (a === undefined) return 1;
+      if (b === undefined) return -1;
+      return a.localeCompare(b);
+    });
+
+    const severityOrder = {error: 0, warning: 1, suggestion: 2} as const;
+
+    for (const [file, fileMessages] of sortedGroups) {
+      const group = fileMessages
+        .slice()
+        .sort((a, b) => severityOrder[a.severity] - severityOrder[b.severity]);
+      prompts.log.message(styleText('underline', file ?? 'general'), {
+        spacing: 0
+      });
+      for (const msg of group) {
+        prompts.log.message(
+          formatBulletMessage(msg.message, labels[msg.severity]),
+          {spacing: 0}
+        );
       }
       prompts.log.message('', {spacing: 0});
     }
diff --git a/src/test/__snapshots__/custom-manifests.test.ts.snap b/src/test/__snapshots__/custom-manifests.test.ts.snap
index f59f8c9..a6e999d 100644
--- a/src/test/__snapshots__/custom-manifests.test.ts.snap
+++ b/src/test/__snapshots__/custom-manifests.test.ts.snap
@@ -5,26 +5,31 @@ exports[`Custom Manifests > should handle invalid manifest files gracefully 1`]
 exports[`Custom Manifests > should load and use custom manifest files 1`] = `
 [
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-0" can be replaced with inline native syntax. Use picocolors, kleur, or native console styling. See more at https://github.com/e18e/module-replacements/blob/main/docs/modules/fake-0.md.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-1" can be replaced with inline native syntax. Use native JavaScript methods or specific lodash functions.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-2" can be replaced with native functionality. Required Node >= 12.0.0. You can read more at https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Global_Objects/Intl/DateTimeFormat.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-3" can be replaced with a more performant alternative. See more at https://github.com/e18e/module-replacements/blob/main/docs/modules/request-alternatives.md.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-4" can be removed, and native functionality used instead",
     "score": 0,
     "severity": "warning",
@@ -35,36 +40,43 @@ exports[`Custom Manifests > should load and use custom manifest files 1`] = `
 exports[`Custom Manifests > should load multiple manifest files 1`] = `
 [
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-0" can be replaced with inline native syntax. Use picocolors, kleur, or native console styling. See more at https://github.com/e18e/module-replacements/blob/main/docs/modules/fake-0.md.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-1" can be replaced with inline native syntax. Use native JavaScript methods or specific lodash functions.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-2" can be replaced with native functionality. Required Node >= 12.0.0. You can read more at https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Global_Objects/Intl/DateTimeFormat.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-3" can be replaced with a more performant alternative. See more at https://github.com/e18e/module-replacements/blob/main/docs/modules/request-alternatives.md.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-4" can be removed, and native functionality used instead",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-5" can be replaced with inline native syntax. Use Fastify, Koa, or native Node.js http module.",
     "score": 0,
     "severity": "warning",
   },
   {
+    "file": "package.json",
     "message": "Module "@e18e/fake-6" can be removed, and native functionality used instead",
     "score": 0,
     "severity": "warning",
@@ -76,26 +88,31 @@ exports[`Custom Manifests > should prioritize custom replacements over built-in
 {
   "withCustom": [
     {
+      "file": "package.json",
       "message": "Module "@e18e/fake-0" can be replaced with inline native syntax. Use picocolors, kleur, or native console styling. See more at https://github.com/e18e/module-replacements/blob/main/docs/modules/fake-0.md.",
       "score": 0,
       "severity": "warning",
     },
     {
+      "file": "package.json",
       "message": "Module "@e18e/fake-1" can be replaced with inline native syntax. Use native JavaScript methods or specific lodash functions.",
       "score": 0,
       "severity": "warning",
     },
     {
+      "file": "package.json",
       "message": "Module "@e18e/fake-2" can be replaced with native functionality. Required Node >= 12.0.0. You can read more at https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Global_Objects/Intl/DateTimeFormat.",
       "score": 0,
       "severity": "warning",
     },
     {
+      "file": "package.json",
       "message": "Module "@e18e/fake-3" can be replaced with a more performant alternative. See more at https://github.com/e18e/module-replacements/blob/main/docs/modules/request-alternatives.md.",
       "score": 0,
       "severity": "warning",
     },
     {
+      "file": "package.json",
       "message": "Module "@e18e/fake-4" can be removed, and native functionality used instead",
       "score": 0,
       "severity": "warning",
diff --git a/src/test/analyze/__snapshots__/web-features-codemods.test.ts.snap b/src/test/analyze/__snapshots__/web-features-codemods.test.ts.snap
index 1dc544a..e11d21c 100644
--- a/src/test/analyze/__snapshots__/web-features-codemods.test.ts.snap
+++ b/src/test/analyze/__snapshots__/web-features-codemods.test.ts.snap
@@ -3,7 +3,8 @@
 exports[`runWebFeaturesCodemodsAnalysis > handles a file with multiple matches 1`] = `
 [
   {
-    "message": "File "index.js" can use newer web features: arrayAt, exponentiation.",
+    "file": "index.js",
+    "message": "Can use newer web features: arrayAt, exponentiation.",
     "score": 0,
     "severity": "suggestion",
   },
@@ -15,7 +16,8 @@ exports[`runWebFeaturesCodemodsAnalysis > handles a file with no matches 1`] = `
 exports[`runWebFeaturesCodemodsAnalysis > handles a file with one match 1`] = `
 [
   {
-    "message": "File "index.js" can use newer web features: arrayAt.",
+    "file": "index.js",
+    "message": "Can use newer web features: arrayAt.",
     "score": 0,
     "severity": "suggestion",
   },
@@ -25,7 +27,8 @@ exports[`runWebFeaturesCodemodsAnalysis > handles a file with one match 1`] = `
 exports[`runWebFeaturesCodemodsAnalysis > handles multiple occurrences of the same match in one file 1`] = `
 [
   {
-    "message": "File "index.js" can use newer web features: arrayAt.",
+    "file": "index.js",
+    "message": "Can use newer web features: arrayAt.",
     "score": 0,
     "severity": "suggestion",
   },
@@ -37,7 +40,8 @@ exports[`runWebFeaturesCodemodsAnalysis > ignores a file path outside of the roo
 exports[`runWebFeaturesCodemodsAnalysis > respects the src option 1`] = `
 [
   {
-    "message": "File "src/index.js" can use newer web features: arrayAt.",
+    "file": "src/index.js",
+    "message": "Can use newer web features: arrayAt.",
     "score": 0,
     "severity": "suggestion",
   },
diff --git a/src/test/analyze/core-js.test.ts b/src/test/analyze/core-js.test.ts
index c01b994..a6593d3 100644
--- a/src/test/analyze/core-js.test.ts
+++ b/src/test/analyze/core-js.test.ts
@@ -312,7 +312,7 @@ describe('runCoreJsAnalysis', () => {
     const result = await runCoreJsAnalysis(context);
 
     expect(result.messages).toHaveLength(1);
-    expect(result.messages[0]?.message).toContain('src');
+    expect(result.messages[0]?.file).toContain('src');
   });
 
   it('scans multiple src globs when options.src has more than one entry', async () => {
diff --git a/src/test/cli.test.ts b/src/test/cli.test.ts
index f11f47d..902d2de 100644
--- a/src/test/cli.test.ts
+++ b/src/test/cli.test.ts
@@ -163,7 +163,7 @@ describe('analyze exit codes', () => {
     );
     expect(code).toBe(0);
     const output = stdout + stderr;
-    expect(output).not.toContain('Warnings:');
+    expect(output).not.toContain('warning');
     expect(output).toMatch(/below --report-level error/);
   });
 
@@ -174,8 +174,8 @@ describe('analyze exit codes', () => {
     );
     expect(code).toBe(1);
     const output = stdout + stderr;
-    expect(output).toContain('Warnings:');
-    expect(output).not.toContain('Suggestions:');
+    expect(output).toContain('warning');
+    expect(output).not.toContain('suggestion');
   });
 
   it('--quiet hides non-errors like ESLint (default log-level still fails on warnings)', async () => {
@@ -185,7 +185,7 @@ describe('analyze exit codes', () => {
     );
     expect(code).toBe(1);
     const output = stdout + stderr;
-    expect(output).not.toContain('Warnings:');
+    expect(output).not.toContain('warning');
     expect(output).toContain('hidden by --quiet');
   });
 });
diff --git a/src/types.ts b/src/types.ts
index a39af0c..7d0fbe9 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -33,6 +33,8 @@ export interface Message {
   severity: 'error' | 'warning' | 'suggestion';
   score: number;
   message: string;
+  /** File the message relates to, relative to the project root. */
+  file?: string;
   /** Command that can fix this message (e.g. 'migrate'). */
   fixableBy?: string;
 }