diff --git a/apps/web/app/(app)/[emailAccountId]/assistant/settings/WritingStyleSetting.tsx b/apps/web/app/(app)/[emailAccountId]/assistant/settings/WritingStyleSetting.tsx
index 2a8267a8d1..9e609b5ef4 100644
--- a/apps/web/app/(app)/[emailAccountId]/assistant/settings/WritingStyleSetting.tsx
+++ b/apps/web/app/(app)/[emailAccountId]/assistant/settings/WritingStyleSetting.tsx
@@ -24,8 +24,12 @@ import {
   saveWritingStyleBody,
 } from "@/utils/actions/user.validation";
 import { saveWritingStyleAction } from "@/utils/actions/user";
+import { regenerateWritingStyleAction } from "@/utils/actions/assess";
 import { Tiptap, type TiptapHandle } from "@/components/editor/Tiptap";
 import { getActionErrorMessage } from "@/utils/error";
+import { Loader2, Sparkles } from "lucide-react";
+
+const WRITING_STYLE_MAX_LENGTH = 2000;
 
 export function WritingStyleSetting() {
   const { data, isLoading, error } = useEmailAccountFull();
@@ -69,24 +73,48 @@ function WritingStyleDialog({
     control,
     formState: { errors },
     handleSubmit,
+    setValue,
   } = useForm<SaveWritingStyleBody>({
     defaultValues: { writingStyle: currentWritingStyle },
     resolver: zodResolver(saveWritingStyleBody),
   });
 
+  // --- REGENERATE ACTION ---
+  const { execute: generate, isExecuting: isGenerating } = useAction(
+    regenerateWritingStyleAction.bind(null, emailAccountId),
+    {
+      onSuccess: (data) => {
+        const rawStyle = data?.data?.writingStyle;
+
+        if (rawStyle) {
+          // Truncate to ensure it passes the save validation schema
+          const safeStyle = rawStyle.slice(0, WRITING_STYLE_MAX_LENGTH);
+
+          setValue("writingStyle", safeStyle);
+          if (editorRef.current?.editor) {
+            editorRef.current.editor.commands.setContent(safeStyle);
+          }
+          toastSuccess({ description: "Writing style regenerated!" });
+        } else {
+          toastSuccess({ description: "Not enough data to generate style." });
+        }
+      },
+      onError: (error) => {
+        toastError({ description: getActionErrorMessage(error.error) });
+      },
+    },
+  );
+  // -------------------------
+
   const { execute, isExecuting } = useAction(
     saveWritingStyleAction.bind(null, emailAccountId),
     {
       onSuccess: () => {
-        toastSuccess({
-          description: "Writing style saved!",
-        });
+        toastSuccess({ description: "Writing style saved!" });
         setOpen(false);
       },
       onError: (error) => {
-        toastError({
-          description: getActionErrorMessage(error.error),
-        });
+        toastError({ description: getActionErrorMessage(error.error) });
       },
       onSettled: () => {
         mutate();
@@ -120,7 +148,7 @@ function WritingStyleDialog({
                   initialContent={field.value ?? ""}
                   onChange={field.onChange}
                   output="markdown"
-                  className="prose prose-sm dark:prose-invert max-w-none [&_p.is-editor-empty:first-child::before]:pointer-events-none [&_p.is-editor-empty:first-child::before]:float-left [&_p.is-editor-empty:first-child::before]:h-0 [&_p.is-editor-empty:first-child::before]:text-muted-foreground [&_p.is-editor-empty:first-child::before]:content-[attr(data-placeholder)]"
+                  className="prose prose-sm dark:prose-invert max-w-none"
                   autofocus={false}
                   preservePastedLineBreaks
                   placeholder={`Typical Length: 2-3 sentences
@@ -142,9 +170,26 @@ Notable Traits:
               {errors.writingStyle.message}
             </p>
           )}
-          <Button type="submit" className="mt-4" loading={isExecuting}>
-            Save
-          </Button>
+
+          <div className="flex justify-end gap-3 mt-4">
+            <Button
+              type="button"
+              variant="outline"
+              onClick={() => generate()}
+              disabled={isGenerating || isExecuting}
+            >
+              {isGenerating ? (
+                <Loader2 className="mr-2 h-4 w-4 animate-spin" />
+              ) : (
+                <Sparkles className="mr-2 h-4 w-4" />
+              )}
+              {isGenerating ? "Generating..." : "Regenerate Style"}
+            </Button>
+
+            <Button type="submit" loading={isExecuting} disabled={isGenerating}>
+              Save
+            </Button>
+          </div>
         </form>
       </DialogContent>
     </Dialog>
diff --git a/apps/web/utils/actions/assess.ts b/apps/web/utils/actions/assess.ts
index 255e12ef45..a8fb5ca865 100644
--- a/apps/web/utils/actions/assess.ts
+++ b/apps/web/utils/actions/assess.ts
@@ -97,3 +97,55 @@ export const analyzeWritingStyleAction = actionClient
 
     return { success: true };
   });
+
+export const regenerateWritingStyleAction = actionClient
+  .metadata({ name: "regenerateWritingStyle" })
+  .action(async ({ ctx: { emailAccountId, provider, logger } }) => {
+    const emailAccount = await prisma.emailAccount.findUnique({
+      where: { id: emailAccountId },
+      select: {
+        id: true,
+        userId: true,
+        email: true,
+        about: true,
+        multiRuleSelectionEnabled: true,
+        timezone: true,
+        calendarBookingLink: true,
+        user: { select: { aiProvider: true, aiModel: true, aiApiKey: true } },
+      },
+    });
+
+    if (!emailAccount) throw new SafeError("Email account not found");
+
+    const emailProvider = await createEmailProvider({
+      emailAccountId,
+      provider,
+      logger,
+    });
+    const sentMessages = await emailProvider.getSentMessages(20);
+
+    const style = await aiAnalyzeWritingStyle({
+      emails: sentMessages.map((email) =>
+        getEmailForLLM(email, { extractReply: true }),
+      ),
+      emailAccount: { ...emailAccount, account: { provider } },
+    });
+
+    if (!style) return { writingStyle: "" };
+
+    const writingStyle = [
+      style.typicalLength ? `Typical Length: ${style.typicalLength}` : null,
+      style.formality ? `Formality: ${style.formality}` : null,
+      style.commonGreeting ? `Common Greeting: ${style.commonGreeting}` : null,
+      style.notableTraits.length
+        ? `Notable Traits: ${formatBulletList(style.notableTraits)}`
+        : null,
+      style.examples.length
+        ? `Examples: ${formatBulletList(style.examples)}`
+        : null,
+    ]
+      .filter(Boolean)
+      .join("\n");
+
+    return { writingStyle };
+  });