diff --git a/apps/web/utils/ai/assistant/chat.ts b/apps/web/utils/ai/assistant/chat.ts
index e0ba397b41..4507e8ff4a 100644
--- a/apps/web/utils/ai/assistant/chat.ts
+++ b/apps/web/utils/ai/assistant/chat.ts
@@ -826,11 +826,19 @@ Examples:
           }
 
           if (patternsToSave.length > 0) {
-            await saveLearnedPatterns({
+            const result = await saveLearnedPatterns({
               emailAccountId,
               ruleName: rule.name,
               patterns: patternsToSave,
             });
+
+            if ("error" in result) {
+              return {
+                success: false,
+                ruleId: rule.id,
+                error: result.error,
+              };
+            }
           }
 
           return { success: true, ruleId: rule.id };
diff --git a/apps/web/utils/rule/learned-patterns.ts b/apps/web/utils/rule/learned-patterns.ts
index 8aeec9eeae..cbb78a7718 100644
--- a/apps/web/utils/rule/learned-patterns.ts
+++ b/apps/web/utils/rule/learned-patterns.ts
@@ -1,6 +1,7 @@
 import prisma from "@/utils/prisma";
 import { createScopedLogger } from "@/utils/logger";
 import { GroupItemType } from "@prisma/client";
+import { isDuplicateError } from "@/utils/prisma-helpers";
 
 const logger = createScopedLogger("rule/learned-patterns");
 
@@ -94,45 +95,81 @@ export async function saveLearnedPatterns({
 
   if (!rule) {
     logger.error("Rule not found", { emailAccountId, ruleName });
-    return;
+    return { error: "Rule not found" };
   }
 
   let groupId = rule.groupId;
 
   if (!groupId) {
-    // Create a new group for this rule if one doesn't exist
-    const newGroup = await prisma.group.create({
-      data: {
-        emailAccountId,
-        name: ruleName,
-        rule: { connect: { id: rule.id } },
-      },
-    });
+    try {
+      const newGroup = await prisma.group.create({
+        data: {
+          emailAccountId,
+          name: ruleName,
+          rule: { connect: { id: rule.id } },
+        },
+      });
 
-    groupId = newGroup.id;
+      groupId = newGroup.id;
+    } catch (error) {
+      if (isDuplicateError(error)) {
+        logger.error("Group already exists", { emailAccountId, ruleName });
+        const newGroup2 = await prisma.group.create({
+          data: {
+            emailAccountId,
+            name: `${ruleName} (${new Date().toISOString()})`,
+            rule: { connect: { id: rule.id } },
+          },
+        });
+        groupId = newGroup2.id;
+      } else {
+        logger.error("Error creating learned patterns group", { error });
+        return { error: "Error creating learned patterns group" };
+      }
+    }
   }
 
+  const errors: string[] = [];
+
   // Process all patterns in a single function
   for (const pattern of patterns) {
     // Store pattern with the exclude flag properly set in the database
     // This maps directly to the new exclude field in the GroupItem model
-    await prisma.groupItem.upsert({
-      where: {
-        groupId_type_value: {
+    try {
+      await prisma.groupItem.upsert({
+        where: {
+          groupId_type_value: {
+            groupId,
+            type: pattern.type,
+            value: pattern.value,
+          },
+        },
+        update: {
+          exclude: pattern.exclude || false,
+        },
+        create: {
           groupId,
           type: pattern.type,
           value: pattern.value,
+          exclude: pattern.exclude || false,
         },
-      },
-      update: {
-        exclude: pattern.exclude || false,
-      },
-      create: {
-        groupId,
-        type: pattern.type,
-        value: pattern.value,
-        exclude: pattern.exclude || false,
-      },
-    });
+      });
+    } catch (error) {
+      const message = `${pattern.value} (${pattern.type}) ${
+        pattern.exclude ? "excluded" : ""
+      }`;
+
+      if (isDuplicateError(error)) {
+        errors.push(`Duplicate pattern: ${message}`);
+      } else {
+        errors.push(`Error saving pattern: ${message}`);
+      }
+    }
   }
+
+  if (errors.length > 0) {
+    return { error: errors.join(", ") };
+  }
+
+  return { success: true };
 }
diff --git a/version.txt b/version.txt
index 35170e7e76..00b0c3d735 100644
--- a/version.txt
+++ b/version.txt
@@ -1 +1 @@
-v1.9.12
\ No newline at end of file
+v1.9.13
\ No newline at end of file