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Fix inbox sender search filtering #2672

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Fix inbox sender search filtering #2672

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195 changes: 160 additions & 35 deletions apps/web/utils/ai/assistant/chat-inbox-tools.test.ts
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Original file line number Diff line number Diff line change
Expand Up @@ -706,10 +706,156 @@ describe("chat inbox tools - bulk pagination guidance (INB-134)", () => {
expect(result.hasMore).toBe(false);
});

it("searchInbox retries Microsoft fielded sender searches with a plain-text fallback", async () => {
it("searchInbox uses exact Outlook sender filtering for fielded sender queries", async () => {
const searchMessages = vi.fn().mockResolvedValue({
messages: [
{
id: "m1",
threadId: "t1",
snippet: "Can you take a look?",
historyId: "",
inline: [],
headers: {
from: "sender@example.com",
to: TEST_EMAIL,
subject: "Review request",
date: "2026-01-01T00:00:00.000Z",
},
subject: "Review request",
textPlain: "",
textHtml: "",
labelIds: [],
internalDate: "0",
},
],
nextPageToken: undefined,
});

(createEmailProvider as any).mockResolvedValue({
searchMessages,
getLabels: vi.fn().mockResolvedValue([]),
});

const toolInstance = searchInboxTool({
email: TEST_EMAIL,
emailAccountId: "email-account-1",
provider: "microsoft",
logger,
});

const result: any = await (toolInstance.execute as any)({
query: "from:sender@example.com",
limit: 20,
});

expect(searchMessages).toHaveBeenCalledWith({
query: "",
fromEmail: "sender@example.com",
maxResults: 20,
pageToken: undefined,
readState: undefined,
labelName: undefined,
});
expect(result.messages).toHaveLength(1);
expect(result.queryUsed).toBe("from:sender@example.com");
});

it("searchInbox uses exact Outlook sender filtering for bare sender email queries", async () => {
const searchMessages = vi.fn().mockResolvedValue({
messages: [
{
id: "m1",
threadId: "t1",
snippet: "Can you take a look?",
historyId: "",
inline: [],
headers: {
from: "Sender <sender@example.com>",
to: TEST_EMAIL,
subject: "Review request",
date: "2026-01-01T00:00:00.000Z",
},
subject: "Review request",
textPlain: "",
textHtml: "",
labelIds: [],
internalDate: "0",
},
],
nextPageToken: "PAGE_TOKEN_2",
});

(createEmailProvider as any).mockResolvedValue({
searchMessages,
getLabels: vi.fn().mockResolvedValue([]),
});

const toolInstance = searchInboxTool({
email: TEST_EMAIL,
emailAccountId: "email-account-1",
provider: "microsoft",
logger,
});

const result: any = await (toolInstance.execute as any)({
query: "sender@example.com",
limit: 20,
});

expect(searchMessages).toHaveBeenCalledWith({
query: "",
fromEmail: "sender@example.com",
maxResults: 20,
pageToken: undefined,
readState: undefined,
labelName: undefined,
});
expect(result.queryUsed).toBe("from:sender@example.com");
expect(result.nextPageToken).toBe("PAGE_TOKEN_2");
expect(result.hasMore).toBe(true);
});

it("searchInbox forwards explicit Outlook sender filters across pages", async () => {
const searchMessages = vi.fn().mockResolvedValue({
messages: [],
nextPageToken: undefined,
});

(createEmailProvider as any).mockResolvedValue({
searchMessages,
getLabels: vi.fn().mockResolvedValue([]),
});

const toolInstance = searchInboxTool({
email: TEST_EMAIL,
emailAccountId: "email-account-1",
provider: "microsoft",
logger,
});

await (toolInstance.execute as any)({
fromEmail: "sender@example.com",
limit: 20,
pageToken: "PAGE_TOKEN_2",
});

expect(searchMessages).toHaveBeenCalledWith({
query: "",
fromEmail: "sender@example.com",
maxResults: 20,
pageToken: "PAGE_TOKEN_2",
readState: undefined,
labelName: undefined,
});
});

it("searchInbox preserves structured Outlook sender filters when skipping empty pages", async () => {
const searchMessages = vi
.fn()
.mockRejectedValueOnce(new Error("Search syntax failed"))
.mockResolvedValueOnce({
messages: [],
nextPageToken: "PAGE_TOKEN_2",
})
.mockResolvedValueOnce({
messages: [
{
Expand All @@ -719,7 +865,7 @@ describe("chat inbox tools - bulk pagination guidance (INB-134)", () => {
historyId: "",
inline: [],
headers: {
from: "sender@example.com",
from: "Sender <sender@example.com>",
to: TEST_EMAIL,
subject: "Review request",
date: "2026-01-01T00:00:00.000Z",
Expand Down Expand Up @@ -752,21 +898,23 @@ describe("chat inbox tools - bulk pagination guidance (INB-134)", () => {
});

expect(searchMessages).toHaveBeenNthCalledWith(1, {
query: "from:sender@example.com",
query: "",
fromEmail: "sender@example.com",
maxResults: 20,
pageToken: undefined,
readState: undefined,
labelName: undefined,
});
expect(searchMessages).toHaveBeenNthCalledWith(2, {
query: '"sender@example.com"',
query: "",
fromEmail: "sender@example.com",
maxResults: 20,
pageToken: undefined,
pageToken: "PAGE_TOKEN_2",
readState: undefined,
labelName: undefined,
});
expect(result.messages).toHaveLength(1);
expect(result.queryUsed).toBe('"sender@example.com"');
expect(result.queryUsed).toBe("from:sender@example.com");
});

it("searchInbox passes structured Outlook category and read-state filters", async () => {
Expand Down Expand Up @@ -1138,45 +1286,22 @@ describe("chat inbox tools - bulk pagination guidance (INB-134)", () => {
});

const result: any = await (toolInstance.execute as any)({
query: "from:sender@example.com",
query: 'from:sender@example.com subject:"weekly report"',
limit: 20,
});

expect(result).toMatchObject({
queryUsed: "from:sender@example.com",
error: "Failed to search inbox",
provider: "microsoft",
microsoftSearchFeedback: {
failureType: "query_failed",
summary:
"Outlook did not return results for the attempted search query. Retry with one simpler Outlook clause at a time.",
fallbackAttempted: true,
likelyCause: "Retry with one simpler Outlook clause at a time.",
removedTerms: [],
retryQueries: [],
},
});
expect(result.microsoftSearchFeedback.attempts).toEqual([
{
query: "from:sender@example.com",
status: 400,
code: "BadRequest",
message: "Unsupported search clause",
},
{
query: '"sender@example.com"',
status: 400,
code: "BadRequest",
message: "Unsupported search clause",
},
{
query: "sender@example.com",
status: 400,
code: "BadRequest",
message: "Unsupported search clause",
},
]);
expect(searchMessages).toHaveBeenCalledTimes(3);
expect(result.microsoftSearchFeedback.attempts.length).toBeGreaterThan(1);
expect(searchMessages).toHaveBeenCalledTimes(
result.microsoftSearchFeedback.attempts.length,
);
});

it("searchInbox suggests concrete simpler retries for complex Microsoft queries", async () => {
Expand Down
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