fix(api): harden broadcast and assistant fallback errors

packages/api/src/router/assistant-tools.ts

@@ -463,11 +463,6 @@ function toAssistantTimelineMutationError(
   error: unknown,
   context: "updateInline" | "applyShift" | "quickAssign" | "batchShift",
 ): AssistantToolErrorResult | null {
-  const allocationNotFound = toAssistantAllocationNotFoundError(error);
-  if (allocationNotFound && (context === "updateInline" || context === "batchShift")) {
-    return allocationNotFound;
-  }
-
   if (error instanceof TRPCError) {
     if (error.code === "NOT_FOUND") {
       if (error.message.includes("Resource not found")) {
@@ -489,6 +484,11 @@ function toAssistantTimelineMutationError(
     }
   }
 
+  const allocationNotFound = toAssistantAllocationNotFoundError(error);
+  if (allocationNotFound && (context === "updateInline" || context === "batchShift")) {
+    return allocationNotFound;
+  }
+
   const prismaError = getPrismaRequestErrorMetadata(error);
   if (!prismaError) {
     return null;
@@ -1115,21 +1115,11 @@ function toAssistantEstimateMutationError(
     return null;
   }
 
-  const errorText = `${prismaError.message} ${prismaError.metaText}`.toLowerCase();
-  if (errorText.includes("project")) {
-    return { error: "Project not found with the given criteria." };
-  }
-  if (errorText.includes("estimatedemandline") || errorText.includes("estimate_demand_line") || errorText.includes("estimate demand line")) {
-    return { error: "Estimate demand line not found with the given criteria." };
-  }
-  if (errorText.includes("estimateversion") || errorText.includes("estimate_version") || errorText.includes("estimate version")) {
-    return { error: "Estimate version not found with the given criteria." };
-  }
-  if (errorText.includes("estimate")) {
-    return { error: "Estimate not found with the given criteria." };
-  }
-
   if (prismaError.code === "P2003") {
+    const errorText = `${prismaError.message} ${prismaError.metaText}`.toLowerCase();
+    if (errorText.includes("project")) {
+      return { error: "Project not found with the given criteria." };
+    }
     if (errorText.includes("role")) {
       return { error: "Role not found with the given criteria." };
     }
@@ -1139,9 +1129,20 @@ function toAssistantEstimateMutationError(
     if (errorText.includes("scopeitem") || errorText.includes("scope_item") || errorText.includes("scope item")) {
       return { error: "Estimate scope item not found with the given criteria." };
     }
+    return { error: "One of the referenced project, role, resource, or scope items no longer exists." };
   }
 
   if (prismaError.code === "P2025") {
+    const errorText = `${prismaError.message} ${prismaError.metaText}`.toLowerCase();
+    if (errorText.includes("estimatedemandline") || errorText.includes("estimate_demand_line") || errorText.includes("estimate demand line")) {
+      return { error: "Estimate demand line not found with the given criteria." };
+    }
+    if (errorText.includes("estimateversion") || errorText.includes("estimate_version") || errorText.includes("estimate version")) {
+      return { error: "Estimate version not found with the given criteria." };
+    }
+    if (errorText.includes("estimate")) {
+      return { error: "Estimate not found with the given criteria." };
+    }
     switch (action) {
       case "generateWeeklyPhasing":
         return { error: "Estimate demand line not found with the given criteria." };
@@ -1631,19 +1632,97 @@ function getPrismaRequestErrorMetadata(error: unknown): {
   return null;
 }
 
+function getTrpcErrorMetadata(error: unknown): {
+  code: string;
+  message: string;
+} | null {
+  const queue: unknown[] = [error];
+  const visited = new Set<unknown>();
+
+  while (queue.length > 0) {
+    const current = queue.shift();
+    if (current === undefined || current === null || visited.has(current)) {
+      continue;
+    }
+    visited.add(current);
+
+    if (current instanceof TRPCError) {
+      return {
+        code: current.code,
+        message: current.message,
+      };
+    }
+
+    if (typeof current !== "object") {
+      continue;
+    }
+
+    const candidate = current as {
+      code?: unknown;
+      message?: unknown;
+      cause?: unknown;
+      data?: { code?: unknown };
+      shape?: { code?: unknown; message?: unknown };
+    };
+
+    const candidateCode = typeof candidate.code === "string"
+      ? candidate.code
+      : typeof candidate.data?.code === "string"
+        ? candidate.data.code
+        : typeof candidate.shape?.code === "string"
+          ? candidate.shape.code
+          : null;
+    const candidateMessage = typeof candidate.message === "string"
+      ? candidate.message
+      : typeof candidate.shape?.message === "string"
+        ? candidate.shape.message
+        : "";
+
+    if (candidateCode && /^[A-Z_]+$/.test(candidateCode)) {
+      return {
+        code: candidateCode,
+        message: candidateMessage,
+      };
+    }
+
+    if ("cause" in candidate) {
+      queue.push(candidate.cause);
+    }
+  }
+
+  return null;
+}
+
 function toAssistantNotificationCreationError(
   error: unknown,
   context: "notification" | "task" | "broadcast",
 ): AssistantToolErrorResult | null {
+  const trpcError = getTrpcErrorMetadata(error);
+
   if (
     context === "broadcast"
-    && error instanceof TRPCError
-    && error.code === "BAD_REQUEST"
-    && error.message === "No recipients matched the broadcast target."
+    && trpcError?.code === "BAD_REQUEST"
+    && trpcError.message === "No recipients matched the broadcast target."
   ) {
     return { error: "No recipients matched the broadcast target." };
   }
 
+  if (trpcError?.code === "NOT_FOUND") {
+    if (trpcError.message.includes("Sender user not found")) {
+      return { error: "Sender user not found with the given criteria." };
+    }
+    if (trpcError.message.includes("Assignee user not found")) {
+      return { error: "Assignee user not found with the given criteria." };
+    }
+    if (trpcError.message.includes("recipient")) {
+      return context === "broadcast"
+        ? { error: "Broadcast recipient user not found with the given criteria." }
+        : context === "task"
+          ? { error: "Task recipient user not found with the given criteria." }
+          : { error: "Notification recipient user not found with the given criteria." };
+    }
+  }
+
   const prismaError = getPrismaRequestErrorMetadata(error);
   if (!prismaError) {
     return null;
@@ -1681,20 +1760,21 @@ function normalizeAssistantExecutionError(
     return { error: error.message };
   }
 
-  if (error instanceof TRPCError) {
-    if (error.code === "INTERNAL_SERVER_ERROR") {
+  const trpcError = getTrpcErrorMetadata(error);
+  if (trpcError) {
+    if (trpcError.code === "INTERNAL_SERVER_ERROR") {
       return {
         error: "The tool could not complete due to an internal error.",
       };
     }
 
-    if (error.code === "UNAUTHORIZED") {
+    if (trpcError.code === "UNAUTHORIZED") {
       return {
         error: "Authentication is required to use this tool.",
       };
     }
 
-    if (error.code === "FORBIDDEN") {
+    if (trpcError.code === "FORBIDDEN") {
       return {
         error: "You do not have permission to perform this action.",
       };