diff --git a/frontend/src/__tests__/api/tasksApi.test.ts b/frontend/src/__tests__/api/tasksApi.test.ts
index ec682be..d04c3fb 100644
--- a/frontend/src/__tests__/api/tasksApi.test.ts
+++ b/frontend/src/__tests__/api/tasksApi.test.ts
@@ -229,6 +229,7 @@ TASK DETAILS
 
 INSTRUCTIONS
 - Write exactly one email message.
+- The message must be written by Milton Fiscal (Director of Ceremonial Logistics) as the sender persona.
 - Use an extremely formal corporate tone.
 - Keep the content casual, mundane, and slightly nonsensical.
 - Reflect the entity personality and task prompt faithfully.
diff --git a/frontend/src/__tests__/pages/CreateTaskPage.test.tsx b/frontend/src/__tests__/pages/CreateTaskPage.test.tsx
index 5c94f72..eba692b 100644
--- a/frontend/src/__tests__/pages/CreateTaskPage.test.tsx
+++ b/frontend/src/__tests__/pages/CreateTaskPage.test.tsx
@@ -39,11 +39,6 @@ const mockEntity = {
 
 describe('CreateTaskPage', () => {
   beforeEach(() => {
-    vi.mocked(tasksApi.getEmailLookbackLabel).mockReturnValue('Last week')
-    vi.mocked(tasksApi.buildTaskPreviewPrompt).mockImplementation(
-      (entity, task) =>
-        `PROMPT FOR ${entity.name}: ${task.name} | ${task.prompt} | ${task.scheduleCron} | ${task.emailLookback}`
-    )
     vi.mocked(entitiesApi.getEntity).mockResolvedValue(mockEntity)
     mockNavigate.mockClear()
   })
@@ -54,25 +49,36 @@ describe('CreateTaskPage', () => {
     await screen.findByRole('link', { name: /back to entity a/i })
 
     expect(screen.getByLabelText(/task name/i)).toBeInTheDocument()
-    expect(screen.getByLabelText(/task prompt/i)).toBeInTheDocument()
+    expect(screen.queryByLabelText(/task prompt/i)).not.toBeInTheDocument()
     expect(screen.getByLabelText(/^Email Period$/i)).toBeInTheDocument()
     expect(screen.getByLabelText(/^Minute$/i)).toBeInTheDocument()
     expect(screen.getByLabelText(/^Hour$/i)).toBeInTheDocument()
     expect(screen.getByLabelText(/^Day of Month$/i)).toBeInTheDocument()
     expect(screen.getByLabelText(/^Month$/i)).toBeInTheDocument()
     expect(screen.getByLabelText(/^Day of Week$/i)).toBeInTheDocument()
+    expect(screen.queryByRole('button', { name: /generate test message/i })).not.toBeInTheDocument()
+    expect(screen.queryByText(/Final Prompt/i)).not.toBeInTheDocument()
   })
 
-  it('should_generatePreviewAndCreateTask_when_formSubmitted', async () => {
-    vi.mocked(tasksApi.generateTaskPreview).mockResolvedValue('SUBJECT: Preview\nBODY:\nFormal nonsense')
+  it('should_createInactiveTaskAndNavigateToEditTask_when_formSubmitted', async () => {
     vi.mocked(tasksApi.createTask).mockResolvedValue({
       id: 'task-2',
       entityId: 'entity-1',
       name: 'Morning Blast',
-      prompt: 'Talk about coffee',
+      prompt: '',
       scheduleCron: '0 8 * * 1-5',
       emailLookback: 'last_week',
-      active: true,
+      active: false,
+      createdAt: '2026-03-26T10:00:00Z',
+    })
+    vi.mocked(tasksApi.inactivateTask).mockResolvedValue({
+      id: 'task-2',
+      entityId: 'entity-1',
+      name: 'Morning Blast',
+      prompt: '',
+      scheduleCron: '0 8 * * 1-5',
+      emailLookback: 'last_week',
+      active: false,
       createdAt: '2026-03-26T10:00:00Z',
     })
 
@@ -97,45 +103,10 @@ describe('CreateTaskPage', () => {
     expect(screen.getByRole('button', { name: /Monthly/i })).toBeInTheDocument()
 
     fireEvent.change(screen.getByLabelText(/task name/i), { target: { value: 'Morning Blast' } })
-    fireEvent.change(screen.getByLabelText(/task prompt/i), { target: { value: 'Talk about coffee' } })
 
     fireEvent.click(screen.getByRole('button', { name: /Weekdays/i }))
     fireEvent.change(screen.getByLabelText(/^Hour$/i), { target: { value: '8' } })
 
-    expect(screen.getByText(/Final Prompt/i)).toBeInTheDocument()
-    expect(
-      screen.getByText('PROMPT FOR Entity A: Morning Blast | Talk about coffee | 0 8 * * 1-5 | last_week')
-    ).toBeInTheDocument()
-
-    fireEvent.click(screen.getByRole('button', { name: /generate test message/i }))
-
-    await waitFor(() => {
-      expect(tasksApi.generateTaskPreview).toHaveBeenCalled()
-      expect(vi.mocked(tasksApi.buildTaskPreviewPrompt)).toHaveBeenCalledWith(
-        mockEntity,
-        expect.objectContaining({
-          entityId: 'entity-1',
-          name: 'Morning Blast',
-          prompt: 'Talk about coffee',
-          scheduleCron: '0 8 * * 1-5',
-          emailLookback: 'last_week',
-        })
-      )
-      expect(vi.mocked(tasksApi.generateTaskPreview).mock.calls[0][0]).toEqual(
-        expect.objectContaining({
-          entity: mockEntity,
-          task: expect.objectContaining({
-            entityId: 'entity-1',
-            name: 'Morning Blast',
-            prompt: 'Talk about coffee',
-            scheduleCron: '0 8 * * 1-5',
-            emailLookback: 'last_week',
-          }),
-        })
-      )
-      expect(screen.getByText(/Formal nonsense/i)).toBeInTheDocument()
-    })
-
     fireEvent.click(screen.getByRole('button', { name: /create task/i }))
 
     await waitFor(() => {
@@ -144,32 +115,13 @@ describe('CreateTaskPage', () => {
         expect.objectContaining({
           entityId: 'entity-1',
           name: 'Morning Blast',
-          prompt: 'Talk about coffee',
+          prompt: '',
           scheduleCron: '0 8 * * 1-5',
           emailLookback: 'last_week',
         })
       )
-      expect(mockNavigate).toHaveBeenCalledWith('/entities/entity-1')
-    })
-  })
-
-  it('should_showReadablePreviewError_when_generationFails', async () => {
-    vi.mocked(tasksApi.generateTaskPreview).mockRejectedValue(
-      new Error('Unable to generate a test message from the local model. Connection refused')
-    )
-
-    render(<CreateTaskPage />, { wrapper })
-    await screen.findByRole('link', { name: /back to entity a/i })
-
-    fireEvent.change(screen.getByLabelText(/task name/i), { target: { value: 'Morning Blast' } })
-    fireEvent.change(screen.getByLabelText(/task prompt/i), { target: { value: 'Talk about coffee' } })
-
-    fireEvent.click(screen.getByRole('button', { name: /generate test message/i }))
-
-    await waitFor(() => {
-      expect(
-        screen.getByText(/Unable to generate a test message from the local model. Connection refused/i)
-      ).toBeInTheDocument()
+      expect(tasksApi.inactivateTask).toHaveBeenCalledWith('task-2')
+      expect(mockNavigate).toHaveBeenCalledWith('/entities/entity-1/tasks/task-2')
     })
   })
 
diff --git a/frontend/src/__tests__/pages/EditTaskPage.test.tsx b/frontend/src/__tests__/pages/EditTaskPage.test.tsx
index 5462e79..f1c36a7 100644
--- a/frontend/src/__tests__/pages/EditTaskPage.test.tsx
+++ b/frontend/src/__tests__/pages/EditTaskPage.test.tsx
@@ -186,6 +186,59 @@ describe('EditTaskPage', () => {
     })
   })
 
+  it('should_renderGeneratedMessagePanels_when_pageLoads', async () => {
+    renderPage()
+
+    await screen.findByRole('link', { name: /back to entity a/i })
+
+    expect(screen.getByText(/Final Prompt/i)).toBeInTheDocument()
+    expect(screen.getByText(/^Generated Message$/i)).toBeInTheDocument()
+    expect(screen.getByText(/^Generated Message History$/i)).toBeInTheDocument()
+    expect(screen.getByText(/Generate a message and it will appear here./i)).toBeInTheDocument()
+    expect(screen.getByRole('list', { name: /generated message history/i })).toBeInTheDocument()
+    expect(screen.getByText(/No generated messages yet./i)).toBeInTheDocument()
+  })
+
+  it('should_showAndManageGeneratedMessageHistory_when_multipleMessagesGenerated', async () => {
+    vi.mocked(tasksApi.generateTaskPreview)
+      .mockResolvedValueOnce('SUBJECT: First\nBODY:\nFirst output')
+      .mockResolvedValueOnce('SUBJECT: Second\nBODY:\nSecond output')
+
+    renderPage()
+    await screen.findByRole('link', { name: /back to entity a/i })
+
+    const generateButton = screen.getByRole('button', { name: /generate test message/i })
+
+    fireEvent.click(generateButton)
+    await screen.findByText(/First output/i)
+
+    fireEvent.click(generateButton)
+
+    await waitFor(() => {
+      expect(screen.getByText(/Second output/i)).toBeInTheDocument()
+    })
+
+    const history = screen.getByRole('list', { name: /generated message history/i })
+    expect(history).toBeInTheDocument()
+
+    const firstMessageHistoryItem = screen.getByRole('button', { name: /^message #1$/i })
+    const secondMessageHistoryItem = screen.getByRole('button', { name: /^message #2$/i })
+
+    fireEvent.click(firstMessageHistoryItem)
+    expect(screen.getByText(/First output/i)).toBeInTheDocument()
+
+    fireEvent.click(
+      screen.getByRole('button', {
+        name: /delete message #1/i,
+      })
+    )
+
+    await waitFor(() => {
+      expect(firstMessageHistoryItem).not.toBeInTheDocument()
+      expect(secondMessageHistoryItem).toBeInTheDocument()
+    })
+  })
+
   it('should_renderActivateButton_when_taskIsInactive', async () => {
     renderPage({ task: { ...mockTask, active: false } })
 
diff --git a/frontend/src/__tests__/pages/EntitiesPage.test.tsx b/frontend/src/__tests__/pages/EntitiesPage.test.tsx
index 1321703..9167270 100644
--- a/frontend/src/__tests__/pages/EntitiesPage.test.tsx
+++ b/frontend/src/__tests__/pages/EntitiesPage.test.tsx
@@ -41,6 +41,37 @@ describe('EntitiesPage', () => {
     fireEvent.click(addButton)
     await waitFor(() => {
       expect(screen.getByRole('dialog')).toBeInTheDocument()
+      expect(screen.queryByLabelText(/default email context window/i)).not.toBeInTheDocument()
+    })
+  })
+
+  it('should_submitDefaultContextWindow_when_createEntitySubmitted', async () => {
+    vi.mocked(entitiesApi.getEntities).mockResolvedValue([])
+    vi.mocked(entitiesApi.createEntity).mockResolvedValue(mockEntity)
+
+    render(<EntitiesPage />, { wrapper })
+
+    fireEvent.click(screen.getByRole('button', { name: /add|create|new/i }))
+
+    await waitFor(() => {
+      expect(screen.getByRole('dialog', { name: /create entity/i })).toBeInTheDocument()
+    })
+
+    fireEvent.change(screen.getByLabelText(/entity name/i), { target: { value: 'Test Entity' } })
+    fireEvent.change(screen.getByLabelText(/sender email/i), { target: { value: 'test@condado.com' } })
+    fireEvent.change(screen.getByLabelText(/job title/i), { target: { value: 'Tester' } })
+    fireEvent.change(screen.getByLabelText(/personality notes/i), { target: { value: 'Formal' } })
+    fireEvent.click(screen.getByRole('button', { name: /create/i }))
+
+    await waitFor(() => {
+      expect(entitiesApi.createEntity).toHaveBeenCalled()
+      expect(vi.mocked(entitiesApi.createEntity).mock.calls[0]?.[0]).toEqual({
+        name: 'Test Entity',
+        email: 'test@condado.com',
+        jobTitle: 'Tester',
+        personality: 'Formal',
+        contextWindowDays: 3,
+      })
     })
   })
 
diff --git a/frontend/src/__tests__/pages/EntityDetailPage.test.tsx b/frontend/src/__tests__/pages/EntityDetailPage.test.tsx
index 4bf02c5..3038d2e 100644
--- a/frontend/src/__tests__/pages/EntityDetailPage.test.tsx
+++ b/frontend/src/__tests__/pages/EntityDetailPage.test.tsx
@@ -1,4 +1,4 @@
-import { render, screen, waitFor } from '@testing-library/react'
+import { render, screen, waitFor, fireEvent } from '@testing-library/react'
 import { describe, it, expect, vi } from 'vitest'
 import { MemoryRouter, Route, Routes } from 'react-router-dom'
 import { QueryClient, QueryClientProvider } from '@tanstack/react-query'
@@ -20,6 +20,84 @@ const wrapper = ({ children }: { children: React.ReactNode }) => (
 )
 
 describe('EntityDetailPage', () => {
+  it('should_updateEntity_when_editSubmittedFromDetailPage', async () => {
+    vi.mocked(tasksApi.getEmailLookbackLabel).mockReturnValue('Last week')
+
+    vi.mocked(entitiesApi.getEntity)
+      .mockResolvedValueOnce({
+        id: 'entity-1',
+        name: 'Entity A',
+        email: 'a@a.com',
+        jobTitle: 'Ops',
+        personality: 'Formal',
+        scheduleCron: '0 9 * * 1',
+        contextWindowDays: 3,
+        active: true,
+        createdAt: '',
+      })
+      .mockResolvedValueOnce({
+        id: 'entity-1',
+        name: 'Entity A Updated',
+        email: 'updated@a.com',
+        jobTitle: 'Operations Lead',
+        personality: 'Still formal',
+        scheduleCron: '0 9 * * 1',
+        contextWindowDays: 5,
+        active: true,
+        createdAt: '',
+      })
+
+    vi.mocked(entitiesApi.updateEntity).mockResolvedValue({
+      id: 'entity-1',
+      name: 'Entity A Updated',
+      email: 'updated@a.com',
+      jobTitle: 'Operations Lead',
+      personality: 'Still formal',
+      scheduleCron: '0 9 * * 1',
+      contextWindowDays: 5,
+      active: true,
+      createdAt: '',
+    })
+    vi.mocked(tasksApi.getTasksByEntity).mockResolvedValue([])
+
+    render(<EntityDetailPage />, { wrapper })
+
+    await waitFor(() => {
+      expect(screen.getByText(/Entity A/i)).toBeInTheDocument()
+    })
+
+    fireEvent.click(screen.getByRole('button', { name: /edit entity/i }))
+
+    await waitFor(() => {
+      expect(screen.getByRole('dialog', { name: /edit entity/i })).toBeInTheDocument()
+      expect(screen.getByLabelText(/entity name/i)).toHaveValue('Entity A')
+      expect(screen.getByLabelText(/sender email/i)).toHaveValue('a@a.com')
+      expect(screen.getByLabelText(/job title/i)).toHaveValue('Ops')
+      expect(screen.getByLabelText(/personality notes/i)).toHaveValue('Formal')
+      expect(screen.queryByLabelText(/default email context window/i)).not.toBeInTheDocument()
+    })
+
+    fireEvent.change(screen.getByLabelText(/entity name/i), { target: { value: 'Entity A Updated' } })
+    fireEvent.change(screen.getByLabelText(/sender email/i), { target: { value: 'updated@a.com' } })
+    fireEvent.change(screen.getByLabelText(/job title/i), { target: { value: 'Operations Lead' } })
+    fireEvent.change(screen.getByLabelText(/personality notes/i), { target: { value: 'Still formal' } })
+
+    fireEvent.click(screen.getByRole('button', { name: /^save$/i }))
+
+    await waitFor(() => {
+      expect(entitiesApi.updateEntity).toHaveBeenCalledWith('entity-1', {
+        name: 'Entity A Updated',
+        email: 'updated@a.com',
+        jobTitle: 'Operations Lead',
+        personality: 'Still formal',
+        contextWindowDays: 3,
+      })
+      expect(screen.queryByRole('dialog', { name: /edit entity/i })).not.toBeInTheDocument()
+      expect(screen.getByRole('heading', { name: /Entity A Updated/i })).toBeInTheDocument()
+      expect(screen.getByText(/Operations Lead - updated@a.com/i)).toBeInTheDocument()
+    })
+  })
+
   it('should_renderEntityAndTasks_when_pageLoads', async () => {
     vi.mocked(tasksApi.getEmailLookbackLabel).mockReturnValue('Last week')
 
diff --git a/frontend/src/api/tasksApi.ts b/frontend/src/api/tasksApi.ts
index 1666bc2..df1c3b5 100644
--- a/frontend/src/api/tasksApi.ts
+++ b/frontend/src/api/tasksApi.ts
@@ -108,6 +108,7 @@ export function buildTaskPreviewPrompt(
     '',
     'INSTRUCTIONS',
     '- Write exactly one email message.',
+    `- The message must be written by ${entity.name} (${entity.jobTitle}) as the sender persona.`,
     '- Use an extremely formal corporate tone.',
     '- Keep the content casual, mundane, and slightly nonsensical.',
     '- Reflect the entity personality and task prompt faithfully.',
diff --git a/frontend/src/pages/CreateTaskPage.tsx b/frontend/src/pages/CreateTaskPage.tsx
index e00341a..16c64d9 100644
--- a/frontend/src/pages/CreateTaskPage.tsx
+++ b/frontend/src/pages/CreateTaskPage.tsx
@@ -3,15 +3,13 @@ import { useMutation, useQuery, useQueryClient } from '@tanstack/react-query'
 import { Link, useNavigate, useParams } from 'react-router-dom'
 import { getEntity } from '../api/entitiesApi'
 import {
-  buildTaskPreviewPrompt,
   createTask,
-  generateTaskPreview,
+  inactivateTask,
   type EmailLookback,
 } from '../api/tasksApi'
 
 interface TaskFormState {
   name: string
-  prompt: string
   scheduleCron: string
   emailLookback: EmailLookback
 }
@@ -72,7 +70,6 @@ function buildCron(parts: CronParts): string {
 
 const DEFAULT_TASK_FORM: TaskFormState = {
   name: '',
-  prompt: '',
   scheduleCron: buildCron(DEFAULT_CRON_PARTS),
   emailLookback: 'last_week',
 }
@@ -83,8 +80,6 @@ export default function CreateTaskPage() {
   const queryClient = useQueryClient()
   const [cronParts, setCronParts] = useState<CronParts>(DEFAULT_CRON_PARTS)
   const [taskForm, setTaskForm] = useState<TaskFormState>(DEFAULT_TASK_FORM)
-  const [preview, setPreview] = useState('')
-  const [previewError, setPreviewError] = useState('')
 
   const { data: entity, isLoading } = useQuery({
     queryKey: ['entity', entityId],
@@ -94,51 +89,18 @@ export default function CreateTaskPage() {
 
   const createTaskMutation = useMutation({
     mutationFn: createTask,
-    onSuccess: async () => {
+    onSuccess: async (createdTask) => {
+      await inactivateTask(createdTask.id)
       await queryClient.invalidateQueries({ queryKey: ['entity-tasks', entityId] })
-      navigate(`/entities/${entityId}`)
-    },
-  })
-
-  const previewMutation = useMutation({
-    mutationFn: generateTaskPreview,
-    onMutate: () => {
-      setPreview('')
-      setPreviewError('')
-    },
-    onSuccess: (value) => setPreview(value),
-    onError: (error) => {
-      setPreviewError(
-        error instanceof Error
-          ? error.message
-          : 'Unable to generate a test message from the local model.'
-      )
+      await queryClient.invalidateQueries({ queryKey: ['entity-task', createdTask.id] })
+      navigate(`/entities/${entityId}/tasks/${createdTask.id}`)
     },
   })
 
   const canSubmit = useMemo(() => {
     const hasFilledCronParts = Object.values(cronParts).every((value) => value.trim().length > 0)
-    return Boolean(taskForm.name.trim() && taskForm.prompt.trim() && hasFilledCronParts)
-  }, [cronParts, taskForm.name, taskForm.prompt])
-
-  const currentTask = useMemo(
-    () => ({
-      entityId,
-      name: taskForm.name,
-      prompt: taskForm.prompt,
-      scheduleCron: taskForm.scheduleCron,
-      emailLookback: taskForm.emailLookback,
-    }),
-    [entityId, taskForm.emailLookback, taskForm.name, taskForm.prompt, taskForm.scheduleCron]
-  )
-
-  const finalPrompt = useMemo(() => {
-    if (!entity) {
-      return 'Entity details unavailable.'
-    }
-
-    return buildTaskPreviewPrompt(entity, currentTask)
-  }, [currentTask, entity])
+    return Boolean(taskForm.name.trim() && hasFilledCronParts)
+  }, [cronParts, taskForm.name])
 
   const applyCronParts = (nextCronParts: CronParts) => {
     setCronParts(nextCronParts)
@@ -186,7 +148,7 @@ export default function CreateTaskPage() {
             createTaskMutation.mutate({
               entityId,
               name: taskForm.name,
-              prompt: taskForm.prompt,
+              prompt: '',
               scheduleCron: taskForm.scheduleCron,
               emailLookback: taskForm.emailLookback,
             })
@@ -205,21 +167,6 @@ export default function CreateTaskPage() {
             />
           </div>
 
-          <div>
-            <label htmlFor="task-prompt" className="text-sm font-medium text-slate-200">
-              Task Prompt
-            </label>
-            <textarea
-              id="task-prompt"
-              value={taskForm.prompt}
-              onChange={(event) =>
-                setTaskForm((prev) => ({ ...prev, prompt: event.target.value }))
-              }
-              className="mt-1 min-h-36 w-full rounded-md border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
-              required
-            />
-          </div>
-
           <div>
             <label htmlFor="task-lookback" className="text-sm font-medium text-slate-200">
               Email Period
@@ -340,47 +287,6 @@ export default function CreateTaskPage() {
             <p className="mt-1 text-xs text-slate-500">Cron: {taskForm.scheduleCron}</p>
           </div>
 
-          <div className="rounded-md border border-slate-800 bg-slate-900 p-4">
-            <button
-              type="button"
-              onClick={() => {
-                if (!canSubmit) return
-                if (!entity) return
-                previewMutation.mutate({ entity, task: currentTask })
-              }}
-              disabled={!canSubmit || previewMutation.isPending}
-              className="rounded-md border border-cyan-500 px-3 py-2 text-sm font-medium text-cyan-300 hover:bg-cyan-500/10 disabled:opacity-50"
-            >
-              {previewMutation.isPending ? 'Generating…' : 'Generate Test Message'}
-            </button>
-
-            <div className="mt-4">
-              <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
-                Final Prompt
-              </p>
-              <pre className="mt-2 whitespace-pre-wrap rounded-md bg-slate-950 p-4 text-xs text-slate-200">
-                {finalPrompt}
-              </pre>
-            </div>
-
-            {previewError && (
-              <p role="alert" className="mt-4 text-sm text-red-300">
-                {previewError}
-              </p>
-            )}
-
-            {preview && (
-              <div className="mt-4">
-                <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
-                  Generated Message
-                </p>
-                <pre className="mt-2 whitespace-pre-wrap rounded-md bg-slate-950 p-4 text-xs text-slate-200">
-                  {preview}
-                </pre>
-              </div>
-            )}
-          </div>
-
           <div className="flex justify-end gap-3 pb-8">
             <button
               type="button"
diff --git a/frontend/src/pages/EditTaskPage.tsx b/frontend/src/pages/EditTaskPage.tsx
index cd251e7..0a37ae9 100644
--- a/frontend/src/pages/EditTaskPage.tsx
+++ b/frontend/src/pages/EditTaskPage.tsx
@@ -1,4 +1,4 @@
-import { useEffect, useMemo, useState } from 'react'
+import { useEffect, useMemo, useRef, useState } from 'react'
 import { useMutation, useQuery, useQueryClient } from '@tanstack/react-query'
 import { Link, useNavigate, useParams } from 'react-router-dom'
 import { getEntity } from '../api/entitiesApi'
@@ -35,6 +35,12 @@ interface RegularitySuggestion {
   cronParts: CronParts
 }
 
+interface GeneratedMessageItem {
+  id: string
+  label: string
+  content: string
+}
+
 const DEFAULT_CRON_PARTS: CronParts = {
   minute: '0',
   hour: '9',
@@ -115,8 +121,10 @@ export default function EditTaskPage() {
   const queryClient = useQueryClient()
   const [cronParts, setCronParts] = useState<CronParts>(DEFAULT_CRON_PARTS)
   const [taskForm, setTaskForm] = useState<TaskFormState>(DEFAULT_TASK_FORM)
-  const [preview, setPreview] = useState('')
+  const [generatedMessages, setGeneratedMessages] = useState<GeneratedMessageItem[]>([])
+  const [selectedMessageId, setSelectedMessageId] = useState('')
   const [previewError, setPreviewError] = useState('')
+  const generatedMessageCounter = useRef(0)
 
   const { data: entity, isLoading: isLoadingEntity } = useQuery({
     queryKey: ['entity', entityId],
@@ -187,10 +195,19 @@ export default function EditTaskPage() {
   const previewMutation = useMutation({
     mutationFn: generateTaskPreview,
     onMutate: () => {
-      setPreview('')
       setPreviewError('')
     },
-    onSuccess: (value) => setPreview(value),
+    onSuccess: (value) => {
+      generatedMessageCounter.current += 1
+      const nextMessage: GeneratedMessageItem = {
+        id: `message-${generatedMessageCounter.current}`,
+        label: `Message #${generatedMessageCounter.current}`,
+        content: value,
+      }
+
+      setGeneratedMessages((prev) => [nextMessage, ...prev])
+      setSelectedMessageId(nextMessage.id)
+    },
     onError: (error) => {
       setPreviewError(
         error instanceof Error
@@ -224,6 +241,11 @@ export default function EditTaskPage() {
     return buildTaskPreviewPrompt(entity, currentTask)
   }, [currentTask, entity])
 
+  const selectedMessage = useMemo(
+    () => generatedMessages.find((message) => message.id === selectedMessageId),
+    [generatedMessages, selectedMessageId]
+  )
+
   const applyCronParts = (nextCronParts: CronParts) => {
     setCronParts(nextCronParts)
     setTaskForm((prev) => ({ ...prev, scheduleCron: buildCron(nextCronParts) }))
@@ -256,7 +278,7 @@ export default function EditTaskPage() {
 
   return (
     <div className="min-h-screen overflow-y-auto bg-slate-950 py-8">
-      <div className="mx-auto max-w-2xl px-4 sm:px-6">
+      <div className="mx-auto max-w-7xl px-4 sm:px-6">
         <nav className="mb-6">
           <Link
             to={`/entities/${entityId}`}
@@ -443,13 +465,72 @@ export default function EditTaskPage() {
               {previewMutation.isPending ? 'Generating…' : 'Generate Test Message'}
             </button>
 
-            <div className="mt-4">
-              <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
-                Final Prompt
-              </p>
-              <pre className="mt-2 whitespace-pre-wrap rounded-md bg-slate-950 p-4 text-xs text-slate-200">
-                {finalPrompt}
-              </pre>
+            <div className="mt-4 grid gap-4 lg:grid-cols-3">
+              <div>
+                <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
+                  Final Prompt
+                </p>
+                <pre className="mt-2 h-full min-h-56 whitespace-pre-wrap rounded-md bg-slate-950 p-4 text-xs text-slate-200">
+                  {finalPrompt}
+                </pre>
+              </div>
+
+              <div>
+                <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
+                  Generated Message
+                </p>
+                <pre className="mt-2 min-h-56 whitespace-pre-wrap rounded-md bg-slate-950 p-4 text-xs text-slate-200">
+                  {selectedMessage?.content ?? 'Generate a message and it will appear here.'}
+                </pre>
+              </div>
+
+              <div>
+                <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
+                  Generated Message History
+                </p>
+                <ul
+                  aria-label="Generated message history"
+                  className="mt-2 space-y-2 rounded-md border border-slate-800 bg-slate-950 p-3"
+                >
+                  {generatedMessages.length === 0 && (
+                    <li className="text-xs text-slate-400">No generated messages yet.</li>
+                  )}
+                  {generatedMessages.map((message) => (
+                    <li
+                      key={message.id}
+                      className="flex items-start gap-2 rounded-md border border-slate-800 bg-slate-900 p-2"
+                    >
+                      <button
+                        type="button"
+                        onClick={() => setSelectedMessageId(message.id)}
+                        className="flex-1 text-left text-xs text-slate-200 hover:text-cyan-300"
+                        aria-label={message.label}
+                      >
+                        <span className="block font-medium">{message.label}</span>
+                        <span className="mt-1 block line-clamp-2 text-slate-400">
+                          {message.content.split('\n')[0]}
+                        </span>
+                      </button>
+                      <button
+                        type="button"
+                        onClick={() => {
+                          setGeneratedMessages((prev) => {
+                            const nextMessages = prev.filter((item) => item.id !== message.id)
+                            if (selectedMessageId === message.id) {
+                              setSelectedMessageId(nextMessages[0]?.id ?? '')
+                            }
+                            return nextMessages
+                          })
+                        }}
+                        className="rounded border border-red-500/40 px-2 py-1 text-[10px] font-semibold uppercase tracking-wide text-red-300 hover:bg-red-500/10"
+                        aria-label={`Delete ${message.label.toLowerCase()}`}
+                      >
+                        Delete
+                      </button>
+                    </li>
+                  ))}
+                </ul>
+              </div>
             </div>
 
             {previewError && (
@@ -458,16 +539,6 @@ export default function EditTaskPage() {
               </p>
             )}
 
-            {preview && (
-              <div className="mt-4">
-                <p className="text-xs font-semibold uppercase tracking-wide text-slate-400">
-                  Generated Message
-                </p>
-                <pre className="mt-2 whitespace-pre-wrap rounded-md bg-slate-950 p-4 text-xs text-slate-200">
-                  {preview}
-                </pre>
-              </div>
-            )}
           </div>
 
           <div className="flex justify-end gap-3 pb-8">
diff --git a/frontend/src/pages/EntitiesPage.tsx b/frontend/src/pages/EntitiesPage.tsx
index ca9c239..0f79c6e 100644
--- a/frontend/src/pages/EntitiesPage.tsx
+++ b/frontend/src/pages/EntitiesPage.tsx
@@ -8,25 +8,29 @@ import {
   VirtualEntityCreateDto,
 } from '../api/entitiesApi'
 
+const DEFAULT_CONTEXT_WINDOW_DAYS = 3
+
+const initialFormState: VirtualEntityCreateDto = {
+  name: '',
+  email: '',
+  jobTitle: '',
+  personality: '',
+  contextWindowDays: DEFAULT_CONTEXT_WINDOW_DAYS,
+}
+
 export default function EntitiesPage() {
   const navigate = useNavigate()
   const queryClient = useQueryClient()
   const { data: entities = [] } = useQuery({ queryKey: ['entities'], queryFn: getEntities })
   const [dialogOpen, setDialogOpen] = useState(false)
-  const [form, setForm] = useState<VirtualEntityCreateDto>({
-    name: '',
-    email: '',
-    jobTitle: '',
-    personality: '',
-    contextWindowDays: 3,
-  })
+  const [form, setForm] = useState<VirtualEntityCreateDto>(initialFormState)
 
   const createMutation = useMutation({
     mutationFn: createEntity,
     onSuccess: (createdEntity) => {
       queryClient.invalidateQueries({ queryKey: ['entities'] })
       setDialogOpen(false)
-      setForm({ name: '', email: '', jobTitle: '', personality: '', contextWindowDays: 3 })
+      setForm(initialFormState)
       navigate(`/entities/${createdEntity.id}`)
     },
   })
@@ -140,20 +144,6 @@ export default function EntitiesPage() {
                   className="block w-full rounded border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
                 />
               </div>
-              <div>
-                <label htmlFor="entity-context-window" className="mb-1 block text-sm font-medium text-slate-200">
-                  Default Email Context Window (days)
-                </label>
-                <input
-                  id="entity-context-window"
-                  type="number"
-                  value={form.contextWindowDays}
-                  onChange={(e) => setForm({ ...form, contextWindowDays: Number(e.target.value) })}
-                  className="block w-full rounded border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
-                  min={1}
-                  required
-                />
-              </div>
               <div className="flex justify-end gap-2 pt-2">
                 <button
                   type="button"
diff --git a/frontend/src/pages/EntityDetailPage.tsx b/frontend/src/pages/EntityDetailPage.tsx
index 670e087..593b896 100644
--- a/frontend/src/pages/EntityDetailPage.tsx
+++ b/frontend/src/pages/EntityDetailPage.tsx
@@ -1,10 +1,24 @@
-import { useQuery } from '@tanstack/react-query'
+import { useMutation, useQuery, useQueryClient } from '@tanstack/react-query'
+import { useState } from 'react'
 import { Link, useParams } from 'react-router-dom'
-import { getEntity } from '../api/entitiesApi'
+import { getEntity, updateEntity, VirtualEntityCreateDto, VirtualEntityResponse } from '../api/entitiesApi'
 import { getEmailLookbackLabel, getTasksByEntity } from '../api/tasksApi'
 
+function toEntityForm(entity: VirtualEntityResponse): VirtualEntityCreateDto {
+  return {
+    name: entity.name,
+    email: entity.email,
+    jobTitle: entity.jobTitle,
+    personality: entity.personality ?? '',
+    contextWindowDays: entity.contextWindowDays,
+  }
+}
+
 export default function EntityDetailPage() {
   const { entityId = '' } = useParams()
+  const queryClient = useQueryClient()
+  const [dialogOpen, setDialogOpen] = useState(false)
+  const [form, setForm] = useState<VirtualEntityCreateDto | null>(null)
 
   const { data: entity, isLoading: isLoadingEntity } = useQuery({
     queryKey: ['entity', entityId],
@@ -18,6 +32,18 @@ export default function EntityDetailPage() {
     enabled: Boolean(entityId),
   })
 
+  const updateMutation = useMutation({
+    mutationFn: (data: VirtualEntityCreateDto) => updateEntity(entityId, data),
+    onSuccess: async () => {
+      await Promise.all([
+        queryClient.invalidateQueries({ queryKey: ['entity', entityId] }),
+        queryClient.invalidateQueries({ queryKey: ['entities'] }),
+      ])
+      setDialogOpen(false)
+      setForm(null)
+    },
+  })
+
   if (!entityId) {
     return <div className="p-8 text-sm text-slate-300">Entity identifier is missing.</div>
   }
@@ -49,12 +75,24 @@ export default function EntityDetailPage() {
             {entity.jobTitle} - {entity.email}
           </p>
         </div>
-        <Link
-          to={`/entities/${entityId}/tasks/new`}
-          className="rounded-md bg-cyan-500 px-4 py-2 text-sm font-semibold text-slate-950 hover:bg-cyan-400"
-        >
-          New Task
-        </Link>
+        <div className="flex items-center gap-3">
+          <button
+            type="button"
+            onClick={() => {
+              setForm(toEntityForm(entity))
+              setDialogOpen(true)
+            }}
+            className="rounded-md border border-slate-700 px-4 py-2 text-sm font-semibold text-slate-100 hover:border-cyan-500 hover:text-cyan-300"
+          >
+            Edit Entity
+          </button>
+          <Link
+            to={`/entities/${entityId}/tasks/new`}
+            className="rounded-md bg-cyan-500 px-4 py-2 text-sm font-semibold text-slate-950 hover:bg-cyan-400"
+          >
+            New Task
+          </Link>
+        </div>
       </div>
 
       <section>
@@ -100,6 +138,93 @@ export default function EntityDetailPage() {
           )}
         </ul>
       </section>
+
+      {dialogOpen && form && (
+        <div
+          role="dialog"
+          aria-modal="true"
+          aria-label="Edit Entity"
+          className="fixed inset-0 z-50 flex items-center justify-center bg-slate-950/70"
+        >
+          <div className="w-full max-w-md rounded-lg border border-slate-800 bg-slate-950 p-6 shadow-lg">
+            <h2 className="mb-4 text-lg font-semibold text-slate-100">Edit Entity</h2>
+            <form
+              onSubmit={(e) => {
+                e.preventDefault()
+                updateMutation.mutate(form)
+              }}
+              className="space-y-3"
+            >
+              <div>
+                <label htmlFor="entity-name" className="mb-1 block text-sm font-medium text-slate-200">
+                  Entity Name
+                </label>
+                <input
+                  id="entity-name"
+                  value={form.name}
+                  onChange={(e) => setForm({ ...form, name: e.target.value })}
+                  className="block w-full rounded border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
+                  required
+                />
+              </div>
+              <div>
+                <label htmlFor="entity-email" className="mb-1 block text-sm font-medium text-slate-200">
+                  Sender Email
+                </label>
+                <input
+                  id="entity-email"
+                  type="email"
+                  value={form.email}
+                  onChange={(e) => setForm({ ...form, email: e.target.value })}
+                  className="block w-full rounded border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
+                  required
+                />
+              </div>
+              <div>
+                <label htmlFor="entity-job-title" className="mb-1 block text-sm font-medium text-slate-200">
+                  Job Title
+                </label>
+                <input
+                  id="entity-job-title"
+                  value={form.jobTitle}
+                  onChange={(e) => setForm({ ...form, jobTitle: e.target.value })}
+                  className="block w-full rounded border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
+                  required
+                />
+              </div>
+              <div>
+                <label htmlFor="entity-personality" className="mb-1 block text-sm font-medium text-slate-200">
+                  Personality Notes
+                </label>
+                <textarea
+                  id="entity-personality"
+                  value={form.personality}
+                  onChange={(e) => setForm({ ...form, personality: e.target.value })}
+                  className="block w-full rounded border border-slate-700 bg-slate-900 px-3 py-2 text-sm text-slate-100"
+                />
+              </div>
+              <div className="flex justify-end gap-2 pt-2">
+                <button
+                  type="button"
+                  onClick={() => {
+                    setDialogOpen(false)
+                    setForm(null)
+                  }}
+                  className="rounded border border-slate-700 px-4 py-2 text-sm text-slate-200"
+                >
+                  Cancel
+                </button>
+                <button
+                  type="submit"
+                  className="rounded bg-cyan-500 px-4 py-2 text-sm font-medium text-slate-950 hover:bg-cyan-400"
+                >
+                  Save
+                </button>
+              </div>
+            </form>
+          </div>
+        </div>
+      )}
     </div>
   )
 }