diff --git a/apps/server/src/services/search/services/lex.spec.ts b/apps/server/src/services/search/services/lex.spec.ts
index 668522b18d7..5b332da04ed 100644
--- a/apps/server/src/services/search/services/lex.spec.ts
+++ b/apps/server/src/services/search/services/lex.spec.ts
@@ -171,6 +171,18 @@ describe("Lexer expression", () => {
         expect(lex(`#!capital ~!neighbor`).expressionTokens.map((t) => t.token)).toEqual(["#!capital", "~!neighbor"]);
     });
 
+    it("fuzzy operators ~= and ~* are tokenized as single operators", () => {
+        // regression: https://github.com/TriliumNext/Trilium/issues/9426
+        expect(lex(`note.title ~= books`).expressionTokens.map((t) => t.token)).toEqual(["note", ".", "title", "~=", "books"]);
+        expect(lex(`note.title ~* books`).expressionTokens.map((t) => t.token)).toEqual(["note", ".", "title", "~*", "books"]);
+        expect(lex(`#author ~= tolkien`).expressionTokens.map((t) => t.token)).toEqual(["#author", "~=", "tolkien"]);
+        expect(lex(`#author ~*'lord of the rings'`).expressionTokens.map((t) => t.token)).toEqual(["#author", "~*", "lord of the rings"]);
+    });
+
+    it("relation prefix still works when ~ is not followed by = or *", () => {
+        expect(lex(`~author.title = Tolkien`).expressionTokens.map((t) => t.token)).toEqual(["~author", ".", "title", "=", "tolkien"]);
+    });
+
     it("negation of sub-expression", () => {
         expect(lex(`# not(#capital) and note.noteId != "root"`).expressionTokens.map((t) => t.token)).toEqual(["#", "not", "(", "#capital", ")", "and", "note", ".", "noteid", "!=", "root"]);
     });
diff --git a/apps/server/src/services/search/services/lex.ts b/apps/server/src/services/search/services/lex.ts
index 2fcd99ca2ad..6d41146d255 100644
--- a/apps/server/src/services/search/services/lex.ts
+++ b/apps/server/src/services/search/services/lex.ts
@@ -106,6 +106,10 @@ function lex(str: string) {
             } else if (["#", "~"].includes(currentWord) && chr === "!") {
                 currentWord += chr;
                 continue;
+            } else if (currentWord === "~" && (chr === "=" || chr === "*")) {
+                // ~= and ~* are fuzzy-match operators, not a relation prefix followed by an operator
+                currentWord += chr;
+                continue;
             } else if (chr === " ") {
                 finishWord(i - 1);
                 continue;