diff --git a/src/debian/deps.rs b/src/debian/deps.rs
index 481c3a4..7dd90e1 100644
--- a/src/debian/deps.rs
+++ b/src/debian/deps.rs
@@ -187,12 +187,16 @@ pub fn parse_simple(dep: &str, build_dep: bool) -> Result<PkgRelation, String> {
 
     let constraint = match (caps.get(5), caps.get(6)) {
         (Some(op), Some(version)) => {
+            // The deprecated single-character spellings `<` and `>` were
+            // "confusingly defined" (Debian Policy §7) to mean earlier-or-equal
+            // and later-or-equal, i.e. `<=` and `>=`; dpkg still accepts them
+            // with those non-strict semantics.
             let relation = match op.as_str() {
-                "<<" | "<" => Relation::Lt,
-                "<=" => Relation::Le,
+                "<<" => Relation::Lt,
+                "<" | "<=" => Relation::Le,
                 "=" => Relation::Eq,
-                ">=" => Relation::Ge,
-                ">>" | ">" => Relation::Gt,
+                ">" | ">=" => Relation::Ge,
+                ">>" => Relation::Gt,
                 other => return Err(format!("invalid relation '{other}' in '{dep}'")),
             };
             let version = DebianVersion::parse(version.as_str())
@@ -1024,6 +1028,56 @@ mod tests {
         assert!(Deps::parse("foo:native", &opts("amd64", &[])).is_ok());
     }
 
+    /// The deprecated single-character operators `<` and `>` mean `<=` and
+    /// `>=` (Debian Policy §7, dpkg behavior), and canonicalize on output.
+    #[test]
+    fn legacy_single_char_relations() {
+        let rel = |dep: &str| {
+            parse_simple(dep, true)
+                .unwrap()
+                .constraint
+                .unwrap()
+                .relation
+        };
+
+        assert_eq!(rel("foo (<< 1.0)"), Relation::Lt);
+        assert_eq!(rel("foo (< 1.0)"), Relation::Le);
+        assert_eq!(rel("foo (<= 1.0)"), Relation::Le);
+        assert_eq!(rel("foo (= 1.0)"), Relation::Eq);
+        assert_eq!(rel("foo (>= 1.0)"), Relation::Ge);
+        assert_eq!(rel("foo (> 1.0)"), Relation::Ge);
+        assert_eq!(rel("foo (>> 1.0)"), Relation::Gt);
+
+        // Rendering always uses the canonical modern spellings.
+        for (dep, rendered) in [
+            ("foo (< 1.0)", "foo (<= 1.0)"),
+            ("foo (> 1.0)", "foo (>= 1.0)"),
+            ("foo (<< 1.0)", "foo (<< 1.0)"),
+            ("foo (>> 1.0)", "foo (>> 1.0)"),
+        ] {
+            assert_eq!(parse_simple(dep, true).unwrap().output(), rendered);
+        }
+    }
+
+    /// `foo (< 1.0)` is satisfied by an installed `foo 1.0` (the legacy
+    /// operator is non-strict); `foo (< 0.9)` is not.
+    #[test]
+    fn legacy_single_char_evaluation() {
+        let mut facts = Facts::new("amd64", "amd64");
+        facts.add_installed("foo", "1.0", "amd64", "no");
+        let o = |s: &str| parse_simple(s, true).unwrap();
+
+        assert_eq!(facts.evaluate_relation(&o("foo (< 1.0)")), Some(true));
+        assert_eq!(facts.evaluate_relation(&o("foo (<= 1.0)")), Some(true));
+        assert_eq!(facts.evaluate_relation(&o("foo (< 0.9)")), Some(false));
+        assert_eq!(facts.evaluate_relation(&o("foo (<< 1.0)")), Some(false));
+
+        assert_eq!(facts.evaluate_relation(&o("foo (> 1.0)")), Some(true));
+        assert_eq!(facts.evaluate_relation(&o("foo (>= 1.0)")), Some(true));
+        assert_eq!(facts.evaluate_relation(&o("foo (> 1.1)")), Some(false));
+        assert_eq!(facts.evaluate_relation(&o("foo (>> 1.0)")), Some(false));
+    }
+
     /// Ported from dpkg `t/Dpkg_Deps.t`: architecture reduction.
     #[test]
     fn arch_reduction() {