diff --git a/apps/desktop/src/lib/__tests__/sql/sqlParameters.spec.ts b/apps/desktop/src/lib/__tests__/sql/sqlParameters.spec.ts
index f1807201e9..265ad7a98e 100644
--- a/apps/desktop/src/lib/__tests__/sql/sqlParameters.spec.ts
+++ b/apps/desktop/src/lib/__tests__/sql/sqlParameters.spec.ts
@@ -877,7 +877,7 @@ describe("substituteSqlParameters", () => {
     ).toBe("select * from t where dt >= '2026-06-26' and amount > 100.50 and enabled = TRUE");
   });
 
-  it("replaces exact quoted braced placeholders as whole tokens without double-quoting", () => {
+  it("preserves single-quoted string contexts for exact braced placeholders", () => {
     const sql = "select * from t where dt = '${date}' and name = \"${name}\" and flag = '#{enabled}' and id = ${id}";
     expect(
       substituteSqlParameters(sql, {
@@ -886,7 +886,29 @@ describe("substituteSqlParameters", () => {
         enabled: { kind: "boolean", value: "true" },
         id: { kind: "number", value: "7" },
       }),
-    ).toBe("select * from t where dt = '2026-06-26' and name = 'O''Reilly' and flag = TRUE and id = 7");
+    ).toBe("select * from t where dt = '2026-06-26' and name = 'O''Reilly' and flag = 'true' and id = 7");
+  });
+
+  it("keeps explicit quotes around raw and numeric parameter values", () => {
+    const sql = "select ${raw_value}, '${raw_value}', ${number_value}, '${number_value}'";
+    expect(
+      substituteSqlParameters(sql, {
+        raw_value: { kind: "raw", value: "current_date" },
+        number_value: { kind: "number", value: "42" },
+      }),
+    ).toBe("select current_date, 'current_date', 42, '42'");
+  });
+
+  it("replaces exact quoted null and empty typed values with SQL NULL", () => {
+    const sql = "select '${null_value}', '${empty_number}', '${empty_raw}', '${empty_string}'";
+    expect(
+      substituteSqlParameters(sql, {
+        null_value: { kind: "null", value: "NULL" },
+        empty_number: { kind: "number", value: "" },
+        empty_raw: { kind: "raw", value: "  " },
+        empty_string: { kind: "string", value: "" },
+      }),
+    ).toBe("select NULL, NULL, NULL, ''");
   });
 
   it("replaces placeholders embedded in ordinary SQL string values", () => {
diff --git a/apps/desktop/src/lib/sql/sqlParameters.ts b/apps/desktop/src/lib/sql/sqlParameters.ts
index aeb6297451..1ca1e782f8 100644
--- a/apps/desktop/src/lib/sql/sqlParameters.ts
+++ b/apps/desktop/src/lib/sql/sqlParameters.ts
@@ -25,7 +25,7 @@ export interface SqlBracedParameter extends SqlParameterDescriptor {
 interface ParameterOccurrence extends SqlParameterDescriptor {
   start: number;
   end: number;
-  replacement?: "string-fragment" | "mybatis-foreach" | "mybatis-where";
+  replacement?: "string-fragment" | "quoted-string" | "mybatis-foreach" | "mybatis-where";
   foreach?: MyBatisForeach;
   where?: MyBatisWhere;
 }
@@ -223,7 +223,7 @@ export function substituteSqlParameters(sql: string, values: Record<string, SqlP
     }
     // Embedded placeholders stay inside the surrounding SQL string, so their value
     // must be escaped as text instead of being wrapped in a second SQL literal.
-    result += occurrence.replacement === "string-fragment" ? sqlParameterStringFragment(input) : sqlParameterLiteral(input);
+    result += occurrence.replacement === "string-fragment" ? sqlParameterStringFragment(input) : occurrence.replacement === "quoted-string" ? sqlParameterQuotedString(input) : sqlParameterLiteral(input);
     cursor = occurrence.end;
   }
   result += sql.slice(cursor);
@@ -428,9 +428,7 @@ function findSqlParameterOccurrences(sql: string, options?: SqlParameterOptions)
     }
 
     if (ch === "'" || ch === '"') {
-      // Exact quoted placeholders use SQL-literal replacement; embedded placeholders
-      // in ordinary single-quoted values use escaped text replacement below.
-      const quoted = tryReadQuotedBracedPlaceholder(sql, i, ch as "'" | '"', isSyntaxEnabled);
+      const quoted = tryReadQuotedBracedPlaceholder(sql, i, ch, isSyntaxEnabled);
       if (quoted) {
         occurrences.push(quoted);
         i = quoted.end;
@@ -1583,6 +1581,7 @@ function tryReadQuotedBracedPlaceholder(sql: string, start: number, quote: "'" |
     name,
     syntax,
     token: sql.slice(start, end),
+    ...(quote === "\'" ? { replacement: "quoted-string" as const } : {}),
     start,
     end,
   };
@@ -1745,6 +1744,11 @@ function sqlParameterStringFragment(input: SqlParameterInput): string {
   return input.value.replace(/'/g, "''");
 }
 
+function sqlParameterQuotedString(input: SqlParameterInput): string {
+  if (input.kind === "null" || ((input.kind === "number" || input.kind === "raw") && !input.value.trim())) return "NULL";
+  return quoteSqlString(input.value);
+}
+
 function normalizeBooleanLiteral(value: string): string {
   const normalized = value.trim().toLowerCase();
   if (normalized === "true" || normalized === "t" || normalized === "yes" || normalized === "y" || normalized === "1") return "TRUE";