diff --git a/packages/server/src/services/data-source-query/execute-query.test.ts b/packages/server/src/services/data-source-query/execute-query.test.ts
index 3fe22569..b53e812a 100644
--- a/packages/server/src/services/data-source-query/execute-query.test.ts
+++ b/packages/server/src/services/data-source-query/execute-query.test.ts
@@ -587,6 +587,64 @@ describe("data source query execution", () => {
     });
   });
 
+  it("does not retry a PostgreSQL query error over plaintext", async () => {
+    const sqlError = Object.assign(
+      new Error("syntax error at or near SELECT"),
+      {
+        code: "42601",
+      }
+    );
+    const { receivedConfigs, runner } = createPostgresRunner([
+      { connectError: sqlError },
+      { rows: [{ result: 1 }] },
+    ]);
+
+    const result = await executePostgresQuery(
+      {
+        ...postgresCredentials,
+        sslMode: "prefer",
+        type: "postgres",
+      },
+      "SELECT broken",
+      undefined,
+      runner
+    );
+
+    expect(result.isErr()).toBe(true);
+    expect(receivedConfigs).toHaveLength(1);
+    expect(receivedConfigs[0]).toMatchObject({
+      ssl: { rejectUnauthorized: true },
+    });
+  });
+
+  it("keeps plaintext fallback for a PostgreSQL connection exception", async () => {
+    const { receivedConfigs, runner } = createPostgresRunner([
+      {
+        connectError: Object.assign(new Error("connection failure"), {
+          code: "08006",
+        }),
+      },
+      { rows: [{ result: 1 }] },
+    ]);
+
+    const rows = unwrapQueryResult(
+      await executePostgresQuery(
+        {
+          ...postgresCredentials,
+          sslMode: "prefer",
+          type: "postgres",
+        },
+        "SELECT 1",
+        undefined,
+        runner
+      )
+    );
+
+    expect(rows).toEqual([{ result: 1 }]);
+    expect(receivedConfigs).toHaveLength(2);
+    expect(receivedConfigs[1]).toMatchObject({ ssl: false });
+  });
+
   it("preserves the prior transport error when plaintext fallback also fails", async () => {
     const initialError = new Error("connection reset by peer");
     const { receivedConfigs, runner } = createPostgresRunner([
diff --git a/packages/server/src/services/data-source-query/postgres-transport.ts b/packages/server/src/services/data-source-query/postgres-transport.ts
index e08381c1..547f1381 100644
--- a/packages/server/src/services/data-source-query/postgres-transport.ts
+++ b/packages/server/src/services/data-source-query/postgres-transport.ts
@@ -69,6 +69,15 @@ export function resolvePostgresFailureTransitions(
     return [];
   }
 
+  // Non-connection SQLSTATE codes mean the server accepted the connection.
+  // Retrying the rejected query on plaintext cannot fix the SQL error and
+  // needlessly sends credentials and the query again over an insecure link.
+  // Class 08 is a connection exception, so keep its transport fallback.
+  const code = readErrorCode(error);
+  if (code && /^[0-9A-Z]{5}$/u.test(code) && !code.startsWith("08")) {
+    return [];
+  }
+
   if (!isTlsVerificationError(error)) {
     return [
       {