diff --git a/.changeset/expire-comment-interaction.md b/.changeset/expire-comment-interaction.md
new file mode 100644
index 00000000..f5f34163
--- /dev/null
+++ b/.changeset/expire-comment-interaction.md
@@ -0,0 +1,5 @@
+---
+'dotenv-diff': patch
+---
+
+fix `@expire` and `--comment-warnings` interaction
diff --git a/packages/cli/src/services/detectEnvExpirations.ts b/packages/cli/src/services/detectEnvExpirations.ts
index 230e3434..16065694 100644
--- a/packages/cli/src/services/detectEnvExpirations.ts
+++ b/packages/cli/src/services/detectEnvExpirations.ts
@@ -27,6 +27,15 @@ export function detectEnvExpirations(filePath: string): ExpireWarning[] {
   for (const raw of lines) {
     const line = raw.trim();
 
+    // A blank line ends the current annotation block. Comments are carried
+    // over (an `@expire` may sit above a documented key), but an empty line
+    // signals "end of block" so a pending annotation cannot leak across a gap
+    // and attach itself to an unrelated key further down the file.
+    if (line === '') {
+      pendingExpire = null;
+      continue;
+    }
+
     const expireMatch = line.match(reg);
 
     if (expireMatch) {
diff --git a/packages/cli/src/services/detectMissingComments.ts b/packages/cli/src/services/detectMissingComments.ts
index 94c4bdb2..b8ff3d59 100644
--- a/packages/cli/src/services/detectMissingComments.ts
+++ b/packages/cli/src/services/detectMissingComments.ts
@@ -2,20 +2,37 @@ import fs from 'fs';
 import type { CommentWarning } from '../config/types.js';
 import { splitEnvLines, parseEnvLine } from '../core/envLine.js';
 
+/**
+ * A line that is *only* an `@expire` annotation, in any of its accepted forms:
+ * `# @expire 2025-12-12`, `// @expire 2025-12-12`, `# expire 2025-12-12`, or a
+ * bare `@expire 2025-12-12`. This is a machine annotation, not human
+ * documentation, so it never satisfies the "documented" rule on its own — but
+ * it is transparent: a real comment sitting above it still documents the key.
+ */
+const BARE_EXPIRE_ANNOTATION =
+  /^(?:\/\/|#)?\s*@?expire\s+\d{4}-\d{2}-\d{2}\s*$/i;
+
 /**
  * Detects `.env.example` keys that lack a documenting comment.
  *
  * A key counts as documented when either:
- *  - the line directly above it is a `#` comment, or
- *  - the key's own line has an inline comment after the value (`KEY=value # ...`).
+ *  - its own line has an inline comment after the value (`KEY=value # ...`), or
+ *  - a real `#` comment sits in the contiguous run of comment/annotation lines
+ *    directly above it. `@expire` annotation lines are transparent (they do not
+ *    themselves document, but they don't hide a real comment above them either);
+ *    a blank line or a non-comment line ends the run.
  *
  * Everything else (a bare `KEY=` with no neighbouring comment) is reported.
  * fx:
  *
  *   # Stripe webhook signing secret
  *   STRIPE_WEBHOOK_SECRET=      ← documented (comment above)
+ *   # Rotated quarterly
+ *   # @expire 2026-12-31
+ *   ROTATING_KEY=              ← documented (comment above the annotation)
  *   PORT=3000 # server port     ← documented (inline comment)
- *   API_KEY=                    ← reported (undocumented)
+ *   # @expire 2026-12-31
+ *   API_KEY=                    ← reported (only an annotation above, no prose)
  *
  * @param filePath - Path to the `.env.example` file to inspect.
  * @returns One warning per undocumented key, in file order.
@@ -33,9 +50,20 @@ export function detectMissingComments(filePath: string): CommentWarning[] {
     const eq = line.indexOf('=');
     const hasInlineComment = eq !== -1 && line.slice(eq + 1).includes('#');
 
-    // Comment directly above: the immediately preceding line is a `#` comment.
-    const prev = i > 0 ? lines[i - 1]!.trim() : '';
-    const hasCommentAbove = prev.startsWith('#');
+    // Comment above: walk up through the contiguous run of lines directly above
+    // the key. `@expire` annotations are skipped over (transparent); the first
+    // real `#` comment documents the key. A blank line or any non-comment line
+    // ends the run — the comment then belongs to something else, not this key.
+    let hasCommentAbove = false;
+    for (let j = i - 1; j >= 0; j--) {
+      const above = lines[j]!.trim();
+      if (above === '') break; // blank line ends the block
+      if (BARE_EXPIRE_ANNOTATION.test(above)) continue; // transparent annotation
+      if (above.startsWith('#')) {
+        hasCommentAbove = true; // a real, prose comment
+      }
+      break; // real comment or a non-comment line (e.g. another key) ends the run
+    }
 
     if (!hasInlineComment && !hasCommentAbove) {
       warnings.push({ key: parsed.key, line: i + 1 });
diff --git a/packages/cli/src/ui/scan/printCommentWarnings.ts b/packages/cli/src/ui/scan/printCommentWarnings.ts
index 90cea180..7f7b0a8b 100644
--- a/packages/cli/src/ui/scan/printCommentWarnings.ts
+++ b/packages/cli/src/ui/scan/printCommentWarnings.ts
@@ -17,7 +17,7 @@ export function printCommentWarnings(
   const rowColor = strict ? error : warning;
 
   console.log();
-  console.log(`${indicator} ${header('Undocumented keys')}`);
+  console.log(`${indicator} ${header('Undocumented keys in .env.example')}`);
   console.log(`${divider}`);
 
   for (const warn of warnings) {
diff --git a/packages/cli/test/unit/services/detectEnvExpirations.test.ts b/packages/cli/test/unit/services/detectEnvExpirations.test.ts
index 7f57b1a4..36f8dd6d 100644
--- a/packages/cli/test/unit/services/detectEnvExpirations.test.ts
+++ b/packages/cli/test/unit/services/detectEnvExpirations.test.ts
@@ -106,6 +106,56 @@ describe('detectEnvExpirations', () => {
     expect(result[0]!.key).toBe('A');
   });
 
+  it('attaches expiration across a comment line to the following key', () => {
+    // A comment between the annotation and the key does not break the link.
+    fs.writeFileSync(
+      envPath,
+      `
+      @expire 2024-12-31
+      # what this key is for
+      API_KEY=123
+      `,
+    );
+
+    const result = detectEnvExpirations(envPath);
+
+    expect(result).toEqual([
+      { key: 'API_KEY', date: '2024-12-31', daysLeft: 30 },
+    ]);
+  });
+
+  it('does not attach expiration across a blank line (blank line ends the block)', () => {
+    // A blank line signals the end of the annotation block, so the annotation
+    // must not leak onto an unrelated key further down.
+    fs.writeFileSync(
+      envPath,
+      `# @expire 2024-12-31
+
+API_KEY=123
+`,
+    );
+
+    const result = detectEnvExpirations(envPath);
+
+    expect(result).toEqual([]);
+  });
+
+  it('does not let an annotation leak across a blank line to a distant key', () => {
+    fs.writeFileSync(
+      envPath,
+      `# @expire 2024-12-31
+# some documentation
+
+# an unrelated section
+DATABASE_URL=postgres://localhost
+`,
+    );
+
+    const result = detectEnvExpirations(envPath);
+
+    expect(result).toEqual([]);
+  });
+
   it('handles multiple expiration blocks', () => {
     fs.writeFileSync(
       envPath,
diff --git a/packages/cli/test/unit/services/detectMissingComments.test.ts b/packages/cli/test/unit/services/detectMissingComments.test.ts
index dcfbb9e0..56c3caed 100644
--- a/packages/cli/test/unit/services/detectMissingComments.test.ts
+++ b/packages/cli/test/unit/services/detectMissingComments.test.ts
@@ -53,4 +53,72 @@ describe('detectMissingComments', () => {
     // The line directly above the key is blank, not a comment.
     expect(run('# note\n\nAPI_KEY=')).toEqual([{ key: 'API_KEY', line: 3 }]);
   });
+
+  it('does not treat a bare @expire annotation above a key as documentation', () => {
+    // An `@expire` annotation is a machine hint, not human docs, so the key
+    // below it is still undocumented and must be reported.
+    expect(run('# @expire 2025-12-12\nAPI_KEY=')).toEqual([
+      { key: 'API_KEY', line: 2 },
+    ]);
+  });
+
+  it('does not treat a bare expire annotation (no @) above a key as documentation', () => {
+    expect(run('# expire 2025-12-12\nAPI_KEY=')).toEqual([
+      { key: 'API_KEY', line: 2 },
+    ]);
+  });
+
+  it('treats a comment that adds prose alongside an expire annotation as documentation', () => {
+    // The comment carries real information beyond the annotation, so it counts.
+    expect(run('# @expire 2025-12-12 rotate before then\nAPI_KEY=')).toEqual(
+      [],
+    );
+  });
+
+  it('accepts a key whose line directly above is a real comment, even with an expire annotation earlier', () => {
+    // Mirrors the user scenario: annotation, then a documenting comment, then
+    // the key. The line directly above the key is a real comment.
+    expect(
+      run('# @expire 2025-12-12\n# what this key is for\nAPI_KEY='),
+    ).toEqual([]);
+  });
+
+  it('sees a real comment above an @expire annotation that sits directly on the key', () => {
+    // The annotation is transparent: a real comment above it still documents
+    // the key, even though the annotation is the line immediately above.
+    expect(
+      run('# Stripe webhook secret\n# @expire 2026-12-31\nSTRIPE_KEY='),
+    ).toEqual([]);
+  });
+
+  it('sees a real comment above a bare (no #) @expire annotation', () => {
+    expect(run('# Expiring secret\n@expire 2025-12-31\nOLD_API_KEY=')).toEqual(
+      [],
+    );
+  });
+
+  it('sees a real comment above a // style @expire annotation', () => {
+    expect(run('# legacy token\n// @expire 2024-01-01\nLEGACY=')).toEqual([]);
+  });
+
+  it('still reports a key when only annotations (no prose) sit above it', () => {
+    // Two annotations and nothing else — no human documentation, so reported.
+    expect(run('# @expire 2026-01-01\n# @expire 2026-02-01\nAPI_KEY=')).toEqual(
+      [{ key: 'API_KEY', line: 3 }],
+    );
+  });
+
+  it('does not let a comment leak across a blank line above the annotation', () => {
+    // Blank line ends the run, so the comment does not document ORPHAN.
+    expect(run('# note\n\n# @expire 2026-01-01\nORPHAN=')).toEqual([
+      { key: 'ORPHAN', line: 4 },
+    ]);
+  });
+
+  it('does not carry a comment across an intervening key line', () => {
+    // `# doc` documents FIRST; SECOND has a key line directly above it.
+    expect(run('# doc\nFIRST=1\nSECOND=2')).toEqual([
+      { key: 'SECOND', line: 3 },
+    ]);
+  });
 });