diff --git a/doc/DATABASE.md b/doc/DATABASE.md
index 5d69f5356e5..e11ddaef860 100644
--- a/doc/DATABASE.md
+++ b/doc/DATABASE.md
@@ -342,6 +342,14 @@ Your Drizzle schema (`packages/db/src/schema/`) stays the same regardless of mod
 
 ## Migration authoring checklist
 
+Older embedded databases can use `SQL_ASCII`. Test encoding-sensitive SQL on
+both `SQL_ASCII` and UTF-8 databases. Migration `0355` constructs its whitespace
+pattern from UTF-8 bytes so legacy databases can compile it, and matches whole
+characters instead of trimming individual bytes. Its shipped hash remains a
+valid migration receipt; otherwise an upgrade could replay its older connector
+triggers over the replacements from `0356`. The encoding migration regression
+checks both selector behavior and preservation of that later trigger definition.
+
 The 0126 issue comment attribution backfill showed the failure mode this checklist is meant to prevent: each batch looked for the next rows with an unindexed predicate, so PostgreSQL repeatedly scanned the same table and the migration became O(n²) as the table grew.
 
 When authoring migrations or one-time backfills:
diff --git a/packages/db/src/client.ts b/packages/db/src/client.ts
index 1f4a9257a39..5efa60e511c 100644
--- a/packages/db/src/client.ts
+++ b/packages/db/src/client.ts
@@ -580,6 +580,9 @@ async function mapHashesToMigrationFiles(migrationFiles: string[]): Promise<Map<
       const content = await readMigrationFileContent(migrationFile);
       const hash = createHash("sha256").update(content).digest("hex");
       mapped.set(hash, migrationFile);
+      if (migrationFile === "0355_agent_tool_definition_hooks.sql") {
+        mapped.set("7ac76adac0220da522c78e51da20490aeb0f90512b4370a05af9f8dd0f75eda6", migrationFile);
+      }
     }),
   );
 
diff --git a/packages/db/src/connector-policy-encoding-migration.test.ts b/packages/db/src/connector-policy-encoding-migration.test.ts
new file mode 100644
index 00000000000..66b1b2068db
--- /dev/null
+++ b/packages/db/src/connector-policy-encoding-migration.test.ts
@@ -0,0 +1,78 @@
+import { createHash } from "node:crypto";
+import { readFile } from "node:fs/promises";
+import postgres from "postgres";
+import { afterAll, beforeAll, describe, expect, it } from "vitest";
+import { applyPendingMigrations, inspectMigrations } from "./client.js";
+import {
+  EMBEDDED_POSTGRES_TEST_TIMEOUT_MS,
+  getEmbeddedPostgresTestSupport,
+  startEmbeddedPostgresTestDatabase,
+  type EmbeddedPostgresTestDatabase,
+} from "./test-embedded-postgres.js";
+
+const support = await getEmbeddedPostgresTestSupport();
+const describePostgres = support.supported ? describe : describe.skip;
+const migration = "0355_agent_tool_definition_hooks.sql";
+const company = "00000000-0000-4000-8000-000000000001";
+const agent = "00000000-0000-4000-8000-000000000002";
+const whitespace = "\t\n\v\f\r \u00a0\u1680\u2000\u2001\u2002\u2003\u2004\u2005\u2006\u2007\u2008\u2009\u200a\u2028\u2029\u202f\u205f\u3000\ufeff";
+
+describePostgres("connector policy migration database encodings", () => {
+  let database: EmbeddedPostgresTestDatabase | undefined;
+  let utf8: ReturnType<typeof postgres> | undefined;
+  let ascii: ReturnType<typeof postgres> | undefined;
+  let asciiUrl: string;
+
+  beforeAll(async () => {
+    database = await startEmbeddedPostgresTestDatabase("paperclip-connector-encoding-");
+    utf8 = postgres(database.connectionString, { max: 1, onnotice: () => {} });
+    await utf8.unsafe("CREATE DATABASE legacy_ascii TEMPLATE template0 ENCODING 'SQL_ASCII' LC_COLLATE 'C' LC_CTYPE 'C'");
+    const url = new URL(database.connectionString);
+    url.pathname = "/legacy_ascii";
+    asciiUrl = url.toString();
+    ascii = postgres(asciiUrl, { max: 1, onnotice: () => {} });
+  }, EMBEDDED_POSTGRES_TEST_TIMEOUT_MS);
+
+  afterAll(async () => {
+    try {
+      await Promise.all([utf8?.end(), ascii?.end()]);
+    } finally {
+      await database?.cleanup();
+    }
+  });
+
+  it.each(["UTF8", "SQL_ASCII"])("migrates %s and matches JavaScript selector trimming", async (encoding) => {
+    const sql = encoding === "UTF8" ? utf8! : ascii!;
+    if (encoding === "SQL_ASCII") await applyPendingMigrations(asciiUrl);
+    expect((await sql`SHOW server_encoding`)[0]?.server_encoding).toBe(encoding);
+    for (const input of [...whitespace, whitespace, `${whitespace}${agent}${whitespace}`, "\u200b", "é", "中"]) {
+      const actual = await sql`SELECT * FROM paperclip_connector_policy_targets(${company}::uuid, ${sql.json({ agentIds: input })})`;
+      expect(Array.from(actual), JSON.stringify(input)).toEqual(input.trim()
+        ? [{ target_type: "agent", target_id: input.trim() }]
+        : [{ target_type: "company", target_id: company }]);
+    }
+    const arrays = await sql`SELECT * FROM paperclip_connector_policy_targets(${company}::uuid,
+      ${sql.json({ agentIds: [whitespace, agent, ` ${agent} `, null, 12] })})`;
+    expect(Array.from(arrays)).toEqual([
+      { target_type: "agent", target_id: agent },
+      { target_type: "agent", target_id: ` ${agent} ` },
+    ]);
+    const intersection = await sql`SELECT * FROM paperclip_connector_policy_targets(${company}::uuid,
+      ${sql.json({ agentId: company, agentIds: [agent] })})`;
+    expect(Array.from(intersection)).toEqual([]);
+  }, EMBEDDED_POSTGRES_TEST_TIMEOUT_MS);
+
+  it("recognizes the shipped receipt without replaying older connector triggers", async () => {
+    const sql = utf8!;
+    const content = await readFile(new URL(`./migrations/${migration}`, import.meta.url), "utf8");
+    const hash = createHash("sha256").update(content).digest("hex");
+    const originalHash = "7ac76adac0220da522c78e51da20490aeb0f90512b4370a05af9f8dd0f75eda6";
+    const before = await sql`SELECT pg_get_functiondef('paperclip_connector_runtime_changed()'::regprocedure) AS definition`;
+    const count = await sql`SELECT count(*)::int AS count FROM drizzle.__drizzle_migrations`;
+    await sql`UPDATE drizzle.__drizzle_migrations SET hash = ${originalHash} WHERE hash = ${hash}`;
+    await applyPendingMigrations(database!.connectionString);
+    expect((await inspectMigrations(database!.connectionString)).status).toBe("upToDate");
+    expect(await sql`SELECT pg_get_functiondef('paperclip_connector_runtime_changed()'::regprocedure) AS definition`).toEqual(before);
+    expect(await sql`SELECT count(*)::int AS count FROM drizzle.__drizzle_migrations`).toEqual(count);
+  }, EMBEDDED_POSTGRES_TEST_TIMEOUT_MS);
+});
diff --git a/packages/db/src/migrations/0355_agent_tool_definition_hooks.sql b/packages/db/src/migrations/0355_agent_tool_definition_hooks.sql
index 2a3bb66d273..00f647a5fb4 100644
--- a/packages/db/src/migrations/0355_agent_tool_definition_hooks.sql
+++ b/packages/db/src/migrations/0355_agent_tool_definition_hooks.sql
@@ -3,13 +3,13 @@ RETURNS TABLE(target_type text, target_id text)
 LANGUAGE plpgsql IMMUTABLE SET search_path = public, pg_temp AS $$
 DECLARE single_agent text := CASE WHEN jsonb_typeof(selectors->'agentId') = 'string' THEN nullif(selectors->>'agentId', '') END;
   many_agents text[];
-  trim_chars text := U&'\0009\000A\000B\000C\000D\0020\00A0\1680\2000\2001\2002\2003\2004\2005\2006\2007\2008\2009\200A\2028\2029\202F\205F\3000\FEFF';
+  trim_pattern text := '[\x09-\x0d ]|' || convert_from(decode('c2a07ce19a807ce280807ce280817ce280827ce280837ce280847ce280857ce280867ce280877ce280887ce280897ce2808a7ce280a87ce280a97ce280af7ce2819f7ce380807cefbbbf', 'hex'), 'UTF8');
 BEGIN
   SELECT array_agg(value#>>'{}') INTO many_agents
     FROM jsonb_array_elements(CASE jsonb_typeof(selectors->'agentIds')
       WHEN 'array' THEN selectors->'agentIds'
-      WHEN 'string' THEN jsonb_build_array(btrim(selectors->>'agentIds', trim_chars)) ELSE '[]'::jsonb END) value
-    WHERE jsonb_typeof(value) = 'string' AND btrim(value#>>'{}', trim_chars) <> '';
+      WHEN 'string' THEN jsonb_build_array(regexp_replace(selectors->>'agentIds', '^(' || trim_pattern || ')+|(' || trim_pattern || ')+$', '', 'g')) ELSE '[]'::jsonb END) value
+    WHERE jsonb_typeof(value) = 'string' AND regexp_replace(value#>>'{}', '^(' || trim_pattern || ')+|(' || trim_pattern || ')+$', '', 'g') <> '';
   IF single_agent IS NOT NULL THEN
     IF coalesce(cardinality(many_agents), 0) = 0 OR single_agent = ANY(many_agents) THEN
       RETURN QUERY SELECT 'agent'::text, single_agent;