diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0b15e11f..803a916f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -301,6 +301,13 @@ per-file diff commands.
   (detail unavailable, synthesised from search)`, documented in the CLI README, and covered
   by automated tests.
 
+- **`verify_pdf.py --ascii-dates` catches the `2016–17` form again** (#698) - the quantity rule from
+  #533 treated `17` as a bare non-year number, so `MSc Physics, 2016–17`, `Sep 2016–17` and
+  `2019–20 season` passed `/apply` Step 5d although the guide says a year on either side of the
+  dash is enough, and all three were caught before #533. A year followed by a two-digit year is
+  now a date pair; `1500–2000` and `2000–5000` stay quantities. Two new `test_verify_pdf.py`
+  cases; the date-pair one fails on master.
+
 ### Security
 
 - **CI no longer leaves the job token in `.git/config` or expands a PR-controlled name into a
diff --git a/tests/test_verify_pdf.py b/tests/test_verify_pdf.py
index 3085cffc..6df55b86 100644
--- a/tests/test_verify_pdf.py
+++ b/tests/test_verify_pdf.py
@@ -134,6 +134,17 @@ class FindNonAsciiDateRangesTests(unittest.TestCase):
             with self.subTest(text=text):
                 self.assertEqual(len(find_non_ascii_date_ranges(text)), 1)
 
+    def test_year_and_two_digit_year_is_a_date_range(self):
+        # The academic-year and season form, caught before the quantity rule
+        # (#533) and suppressed by it because `17` is a bare non-year number.
+        for text in ("MSc Physics, 2016\u201317", "Sep 2016\u201317", "2019\u201320 season", "2016 \u2013 17"):
+            with self.subTest(text=text):
+                self.assertEqual(len(find_non_ascii_date_ranges(text)), 1)
+
+    def test_two_digit_number_before_a_year_is_still_a_quantity(self):
+        # Only year-first is the date form; `17-2016` is not a date anyone writes.
+        self.assertEqual(find_non_ascii_date_ranges("items 17\u20132016"), [])
+
     def test_two_years_joined_by_a_dash_are_still_a_date_range(self):
         for text in ("2016\u20132024", "1990\u20132010 programme", "Roles 2000\u20132024"):
             with self.subTest(text=text):
diff --git a/tools/verify_pdf.py b/tools/verify_pdf.py
index 83782625..9b757f5f 100644
--- a/tools/verify_pdf.py
+++ b/tools/verify_pdf.py
@@ -132,8 +132,18 @@ def _bare_number(token):
     return core
 
 
+_TWO_DIGIT_YEAR = re.compile(r"\d{2}")
+
+
 def _quantity_range(line, dash_index):
-    """True when both sides of the dash are bare numbers and not both years."""
+    """True when both sides of the dash are bare numbers and not a date pair.
+
+    A date pair is two years (`2016-2024`) or a year and a two-digit year
+    (`2016-17`, `2019-20`): the short form is how academic years and seasons
+    are written, and it was caught before the quantity rule existed. Anything
+    else with bare numbers on both sides is a quantity (`1500-2000`,
+    `2000-5000`) and is left alone.
+    """
     before = _TOKEN_BEFORE.search(line[:dash_index])
     after = _TOKEN_AFTER.search(line[dash_index + 1 :])
     if not before or not after:
@@ -141,7 +151,9 @@ def _quantity_range(line, dash_index):
     left, right = _bare_number(before.group(1)), _bare_number(after.group(1))
     if left is None or right is None:
         return False
-    return not (_BARE_YEAR.fullmatch(left) and _BARE_YEAR.fullmatch(right))
+    if _BARE_YEAR.fullmatch(left) and (_BARE_YEAR.fullmatch(right) or _TWO_DIGIT_YEAR.fullmatch(right)):
+        return False
+    return True
 
 
 def find_non_ascii_date_ranges(text):