diff --git a/crates/rest/src/handlers/user_settings.rs b/crates/rest/src/handlers/user_settings.rs
index 4eb8392b7..76c74292a 100644
--- a/crates/rest/src/handlers/user_settings.rs
+++ b/crates/rest/src/handlers/user_settings.rs
@@ -326,22 +326,28 @@ fn parse_if_match(conditional: &ConditionalHeaders) -> RestResult<EntityTagPreco
 }
 
 /// Checks a parsed precondition against the currently stored `version`, where
-/// version `0` means "no document exists yet".
+/// version `0` means "no document has been written yet".
 ///
-/// Version `0` is mapped to "no current representation" so the shared evaluator
-/// gives the semantics this endpoint already had: `*` requires an existing
-/// document, and a concrete tag never matches a document that does not exist.
+/// The GET handler serves that state as a *real representation* — `{}` with
+/// `ETag: "0"` — so the validator it hands out must round-trip: a concrete
+/// `If-Match: "0"` matches version 0, or a fresh user's read-then-conditional-
+/// write could never succeed (#442). `If-Match: *` keeps requiring an actually
+/// stored document, per its "unless it does not exist" semantics.
 fn check_if_match(precondition: &EntityTagPrecondition, version: i64) -> RestResult<()> {
-    let current = (version > 0).then(|| version.to_string());
-    if precondition.if_match_satisfied(current.as_deref()) {
+    let satisfied = match precondition {
+        EntityTagPrecondition::Tags(_) => {
+            precondition.if_match_satisfied(Some(&version.to_string()))
+        }
+        _ => precondition.if_match_satisfied((version > 0).then(|| version.to_string()).as_deref()),
+    };
+    if satisfied {
         return Ok(());
     }
 
-    let message = match current {
-        Some(current) => {
-            format!("If-Match precondition failed: current settings version is {current}")
-        }
-        None => "If-Match precondition failed: no settings document exists yet".to_string(),
+    let message = if version > 0 {
+        format!("If-Match precondition failed: current settings version is {version}")
+    } else {
+        "If-Match precondition failed: no settings document exists yet".to_string()
     };
     Err(RestError::PreconditionFailed { message })
 }
diff --git a/crates/rest/tests/user_settings.rs b/crates/rest/tests/user_settings.rs
index 68d1f90f2..93f7b3604 100644
--- a/crates/rest/tests/user_settings.rs
+++ b/crates/rest/tests/user_settings.rs
@@ -119,6 +119,45 @@ async fn patch_null_deletes_a_key() {
     assert_eq!(get.json::<Value>(), json!({"theme": "dark"}));
 }
 
+/// #442: `GET` serves the empty document as a real representation (`{}` with
+/// `ETag: "0"`), so the validator it hands out must round-trip — a fresh
+/// user's read-then-conditional-write deadlocked on 412 forever otherwise.
+#[tokio::test]
+async fn if_match_zero_writes_the_first_version() {
+    let server = create_test_server();
+
+    let fresh = server.get("/_user/settings").await;
+    assert_eq!(fresh.header("etag"), HeaderValue::from_static("\"0\""));
+
+    let created = server
+        .patch("/_user/settings")
+        .add_header(IF_MATCH, HeaderValue::from_static("\"0\""))
+        .json(&json!({"recentSearches": [{"query": "/Patient?name=x"}]}))
+        .await;
+    created.assert_status_ok();
+    assert_eq!(created.header("etag"), HeaderValue::from_static("\"1\""));
+
+    // And once a version exists, "0" is genuinely stale again.
+    let stale = server
+        .patch("/_user/settings")
+        .add_header(IF_MATCH, HeaderValue::from_static("\"0\""))
+        .json(&json!({"a": 1}))
+        .await;
+    assert_eq!(stale.status_code(), StatusCode::PRECONDITION_FAILED);
+}
+
+/// `If-Match: *` still requires an actually stored document.
+#[tokio::test]
+async fn if_match_star_still_requires_an_existing_document() {
+    let server = create_test_server();
+    let conflict = server
+        .patch("/_user/settings")
+        .add_header(IF_MATCH, HeaderValue::from_static("*"))
+        .json(&json!({"a": 1}))
+        .await;
+    assert_eq!(conflict.status_code(), StatusCode::PRECONDITION_FAILED);
+}
+
 #[tokio::test]
 async fn stale_if_match_is_rejected_with_412() {
     let server = create_test_server();