diff --git a/src/routes/issues.py b/src/routes/issues.py
index d90e16b..82a091c 100644
--- a/src/routes/issues.py
+++ b/src/routes/issues.py
@@ -3,7 +3,7 @@ import json
 from flask import Blueprint, render_template, send_file, redirect, url_for, flash
 
 from app import db
-from src.models import Issue, Article
+from src.models import Issue, Article, Image
 from src.cover import generate_cover
 from src.epub_builder import build_epub
 import config
@@ -112,14 +112,22 @@ def regenerate(issue_id):
         a.title for a in articles_for_issue
         if "Obituaries" not in json.loads(a.categories)
     ]
-    categories_list = []
+
+    image_paths = []
     for a in articles_for_issue:
-        categories_list.extend(json.loads(a.categories))
+        first_image = Image.query.filter_by(article_id=a.id).first()
+        if first_image:
+            image_paths.append(first_image.local_path)
+
+    cover_method = issue.cover_method
+    if cover_method == "ai":
+        issue.cover_method = "mosaic"
+        cover_method = "mosaic"
 
     try:
         cover_path = generate_cover(
-            issue.cover_method, config.ISSUES_DIR,
-            issue.week_start, issue.week_end, headlines, categories_list
+            cover_method, config.ISSUES_DIR,
+            issue.week_start, issue.week_end, headlines, image_paths
         )
         epub_path = build_epub(
             issue.week_start, issue.week_end, article_ids,
diff --git a/tests/test_issues.py b/tests/test_issues.py
new file mode 100644
index 0000000..df2008a
--- /dev/null
+++ b/tests/test_issues.py
@@ -0,0 +1,142 @@
+import json
+import os
+from datetime import date, datetime
+from unittest.mock import MagicMock, patch
+
+from PIL import Image as PILImage
+
+from app import db
+from src.models import Article, Image, Issue
+
+
+def test_regenerate_passes_ordered_image_paths_to_generate_cover(app, client, db, tmp_path):
+    """First image per article, in pub_date order, passed to generate_cover."""
+    os.makedirs(tmp_path, exist_ok=True)
+    img1 = str(tmp_path / "a1.jpg")
+    img2 = str(tmp_path / "a2.jpg")
+    for p in (img1, img2):
+        PILImage.new("RGB", (100, 100), color="blue").save(p, format="JPEG")
+
+    with app.app_context():
+        a1 = Article(
+            guid="g1",
+            title="Earlier Article",
+            author="A",
+            pub_date=datetime(2026, 4, 6, 10, 0),
+            categories=json.dumps(["Government"]),
+            link="http://example.com/1",
+            content_html="<p>x</p>",
+        )
+        a2 = Article(
+            guid="g2",
+            title="Later Article",
+            author="B",
+            pub_date=datetime(2026, 4, 7, 10, 0),
+            categories=json.dumps(["Culture"]),
+            link="http://example.com/2",
+            content_html="<p>y</p>",
+        )
+        db.session.add_all([a1, a2])
+        db.session.flush()
+        db.session.add_all(
+            [
+                Image(
+                    article_id=a1.id,
+                    original_url="https://example.com/1.jpg",
+                    local_path=img1,
+                    width=100,
+                    height=100,
+                ),
+                Image(
+                    article_id=a2.id,
+                    original_url="https://example.com/2.jpg",
+                    local_path=img2,
+                    width=100,
+                    height=100,
+                ),
+            ]
+        )
+        id1, id2 = a1.id, a2.id
+        issue = Issue(
+            week_start=date(2026, 4, 6),
+            week_end=date(2026, 4, 12),
+            cover_method="mosaic",
+            cover_path=str(tmp_path / "old-cover.jpg"),
+            epub_path=str(tmp_path / "old.epub"),
+            article_ids=json.dumps([id2, id1]),
+            status="published",
+        )
+        db.session.add(issue)
+        db.session.commit()
+        issue_id = issue.id
+
+    mock_cover = MagicMock(return_value=str(tmp_path / "new-cover.jpg"))
+    mock_epub = MagicMock(return_value=str(tmp_path / "new.epub"))
+
+    with patch("src.routes.issues.generate_cover", mock_cover), patch(
+        "src.routes.issues.build_epub", mock_epub
+    ):
+        resp = client.post(f"/issues/{issue_id}/regenerate")
+
+    assert resp.status_code in (302, 303)
+    mock_cover.assert_called_once()
+    args = mock_cover.call_args[0]
+    assert args[0] == "mosaic"
+    assert args[4] == ["Earlier Article", "Later Article"]
+    assert args[5] == [img1, img2]
+
+
+def test_regenerate_maps_ai_cover_method_to_mosaic(app, client, db, tmp_path):
+    """Legacy ai issues use mosaic generation and persist cover_method=mosaic."""
+    os.makedirs(tmp_path, exist_ok=True)
+    img1 = str(tmp_path / "a1.jpg")
+    PILImage.new("RGB", (100, 100), color="blue").save(img1, format="JPEG")
+
+    with app.app_context():
+        a1 = Article(
+            guid="g-ai",
+            title="Some Article",
+            author="A",
+            pub_date=datetime(2026, 4, 6, 10, 0),
+            categories=json.dumps(["Government"]),
+            link="http://example.com/1",
+            content_html="<p>x</p>",
+        )
+        db.session.add(a1)
+        db.session.flush()
+        db.session.add(
+            Image(
+                article_id=a1.id,
+                original_url="https://example.com/1.jpg",
+                local_path=img1,
+                width=100,
+                height=100,
+            )
+        )
+        issue = Issue(
+            week_start=date(2026, 4, 6),
+            week_end=date(2026, 4, 12),
+            cover_method="ai",
+            cover_path=str(tmp_path / "old-cover.jpg"),
+            epub_path=str(tmp_path / "old.epub"),
+            article_ids=json.dumps([a1.id]),
+            status="published",
+        )
+        db.session.add(issue)
+        db.session.commit()
+        issue_id = issue.id
+
+    mock_cover = MagicMock(return_value=str(tmp_path / "new-cover.jpg"))
+    mock_epub = MagicMock(return_value=str(tmp_path / "new.epub"))
+
+    with patch("src.routes.issues.generate_cover", mock_cover), patch(
+        "src.routes.issues.build_epub", mock_epub
+    ):
+        client.post(f"/issues/{issue_id}/regenerate")
+
+    mock_cover.assert_called_once()
+    assert mock_cover.call_args[0][0] == "mosaic"
+
+    with app.app_context():
+        updated = db.session.get(Issue, issue_id)
+        assert updated.cover_method == "mosaic"