diff --git a/packages/cli/package.json b/packages/cli/package.json
index 0fb88d97398..11834c47029 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@botpress/cli",
-  "version": "4.17.0",
+  "version": "4.17.1",
   "description": "Botpress CLI",
   "scripts": {
     "build": "pnpm run bundle && pnpm run template:gen",
diff --git a/packages/cli/src/command-implementations/profile-commands.ts b/packages/cli/src/command-implementations/profile-commands.ts
index 4948c378c15..f51bd328d3a 100644
--- a/packages/cli/src/command-implementations/profile-commands.ts
+++ b/packages/cli/src/command-implementations/profile-commands.ts
@@ -5,20 +5,26 @@ import * as errors from '../errors'
 import * as utils from '../utils'
 import { GlobalCache, GlobalCommand, ProfileCredentials } from './global-command'
 
+type ProfileEntry = ProfileCredentials & {
+  name: string
+}
+
 export type ActiveProfileCommandDefinition = typeof commandDefinitions.profiles.subcommands.active
 export class ActiveProfileCommand extends GlobalCommand<ActiveProfileCommandDefinition> {
   public async run(): Promise<void> {
     let activeProfileName = await this.globalCache.get('activeProfile')
 
     if (!activeProfileName) {
-      this.logger.log(`No active profile set, defaulting to ${consts.defaultProfileName}`)
+      this.logger.debug(`No active profile set, defaulting to ${consts.defaultProfileName}`)
       activeProfileName = consts.defaultProfileName
       await this.globalCache.set('activeProfile', activeProfileName)
     }
 
     const profile = await this.readProfileFromFS(activeProfileName)
+    const profileEntry: ProfileEntry = { name: activeProfileName, ...profile }
+
     this.logger.log('Active profile:')
-    this.logger.json({ [activeProfileName]: profile })
+    this.logger.json(profileEntry)
   }
 }
 
@@ -26,14 +32,14 @@ export type ListProfilesCommandDefinition = typeof commandDefinitions.profiles.s
 export class ListProfilesCommand extends GlobalCommand<ListProfilesCommandDefinition> {
   public async run(): Promise<void> {
     const profiles = await this.readProfilesFromFS()
-    if (Object.keys(profiles).length === 0) {
+    const profileEntries: ProfileEntry[] = Object.entries(profiles).map(([name, profile]) => ({ name, ...profile }))
+    if (!profileEntries.length) {
       this.logger.log('No profiles found')
       return
     }
     const activeProfileName = await this.globalCache.get('activeProfile')
-    const profileNames = Object.keys(profiles)
     this.logger.log(`Active profile: '${chalk.bold(activeProfileName)}'`)
-    this.logger.json(profileNames)
+    this.logger.json(profileEntries)
   }
 }
 
diff --git a/plugins/conversation-insights/package.json b/plugins/conversation-insights/package.json
index c610f823546..9a860969683 100644
--- a/plugins/conversation-insights/package.json
+++ b/plugins/conversation-insights/package.json
@@ -2,10 +2,18 @@
   "name": "@botpresshub/conversation-insights",
   "scripts": {
     "check:type": "tsc --noEmit",
-    "build": "bp build"
+    "build": "bp add -y && bp build"
   },
   "private": true,
   "dependencies": {
-    "@botpress/sdk": "workspace:*"
+    "@botpress/sdk": "workspace:*",
+    "json5": "^2.2.3",
+    "jsonrepair": "^3.10.0"
+  },
+  "devDependencies": {
+    "@botpresshub/llm": "workspace:*"
+  },
+  "bpDependencies": {
+    "llm": "../../interfaces/llm"
   }
 }
diff --git a/plugins/conversation-insights/plugin.definition.ts b/plugins/conversation-insights/plugin.definition.ts
index 528f3f6a8ad..7bec41af788 100644
--- a/plugins/conversation-insights/plugin.definition.ts
+++ b/plugins/conversation-insights/plugin.definition.ts
@@ -1,8 +1,12 @@
 import { PluginDefinition, z } from '@botpress/sdk'
+import llm from './bp_modules/llm'
 
 export default new PluginDefinition({
   name: 'conversation-insights',
-  version: '0.1.3',
+  version: '0.2.1',
+  configuration: {
+    schema: z.object({ modelId: z.string() }),
+  },
   conversation: {
     tags: {
       title: { title: 'Title', description: 'The title of the conversation.' },
@@ -18,12 +22,14 @@ export default new PluginDefinition({
         title: 'Participant count',
         description: 'The count of users having participated in the conversation, including the bot. Type: int',
       },
-      isDirty: {
-        title: 'Dirty',
-        description: 'Signifies whether the conversation has had a new message since last refresh',
-      },
     },
   },
-  // TODO: replace this event with a workflow
-  events: { updateTitleAndSummary: { schema: z.object({}) } },
+  events: {
+    updateSummary: {
+      schema: z.object({}),
+    },
+  },
+  interfaces: {
+    llm,
+  },
 })
diff --git a/plugins/conversation-insights/src/generate-content.ts b/plugins/conversation-insights/src/generate-content.ts
new file mode 100644
index 00000000000..91a2d1eae66
--- /dev/null
+++ b/plugins/conversation-insights/src/generate-content.ts
@@ -0,0 +1,34 @@
+import * as sdk from '@botpress/sdk'
+import JSON5 from 'json5'
+import { jsonrepair } from 'jsonrepair'
+import { OutputFormat } from './summary-prompt'
+import * as bp from '.botpress'
+
+export type LLMInput = bp.interfaces.llm.actions.generateContent.input.Input
+export type LLMOutput = bp.interfaces.llm.actions.generateContent.output.Output
+
+export type LLMMessage = LLMInput['messages'][number]
+export type LLMChoice = LLMOutput['choices'][number]
+
+type PredictResponse = {
+  success: boolean
+  json: OutputFormat
+}
+
+const tryParseJson = (str: string) => {
+  try {
+    return JSON5.parse(jsonrepair(str))
+  } catch {
+    return str
+  }
+}
+
+export const parseLLMOutput = (output: LLMOutput): PredictResponse => {
+  const mappedChoices: LLMChoice['content'][] = output.choices.map((choice) => choice.content)
+  if (!mappedChoices[0]) throw new sdk.RuntimeError('Could not parse LLM output')
+  const firstChoice = mappedChoices[0]
+  return {
+    success: true,
+    json: tryParseJson(firstChoice.toString()),
+  }
+}
diff --git a/plugins/conversation-insights/src/index.ts b/plugins/conversation-insights/src/index.ts
index e4aaefbb9b3..172804b2661 100644
--- a/plugins/conversation-insights/src/index.ts
+++ b/plugins/conversation-insights/src/index.ts
@@ -1,42 +1,38 @@
+import * as sdk from '@botpress/sdk'
+import * as summaryUpdater from './summaryUpdater'
+import * as updateScheduler from './summaryUpdateScheduler'
+import * as types from './types'
 import * as bp from '.botpress'
 
+type CommonProps = types.CommonProps
+
 const plugin = new bp.Plugin({
   actions: {},
 })
 
-// TODO: generate a type for CommonProps in the CLI / SDK
-type CommonProps =
-  | bp.HookHandlerProps['after_incoming_message']
-  | bp.HookHandlerProps['after_outgoing_message']
-  | bp.EventHandlerProps
-
 plugin.on.afterIncomingMessage('*', async (props) => {
   const { conversation } = await props.client.getConversation({ id: props.data.conversationId })
-  await _onNewMessage({ ...props, conversation, isDirty: true })
+  const { message_count } = await _onNewMessage({ ...props, conversation })
+
+  if (updateScheduler.isTimeToUpdate(message_count)) {
+    props.client.createEvent({ payload: {}, type: 'updateSummary', conversationId: props.data.conversationId })
+  }
+
   return undefined
 })
 
 plugin.on.afterOutgoingMessage('*', async (props) => {
   const { conversation } = await props.client.getConversation({ id: props.data.message.conversationId })
-  await _onNewMessage({ ...props, conversation, isDirty: false })
+  await _onNewMessage({ ...props, conversation })
   return undefined
 })
 
-plugin.on.event('updateTitleAndSummary', async (props) => {
-  const conversations = await props.client.listConversations({ tags: { isDirty: 'true' } })
-
-  for (const conversation of conversations.conversations) {
-    const messages = await props.client.listMessages({ conversationId: conversation.id })
-    const newMessages = messages.messages.map((message) => message.payload.text)
-    await _updateTitleAndSummary({ ...props, conversationId: conversation.id, messages: newMessages })
-  }
-})
-
 type OnNewMessageProps = CommonProps & {
   conversation: bp.ClientOutputs['getConversation']['conversation']
-  isDirty: boolean
 }
-const _onNewMessage = async (props: OnNewMessageProps) => {
+const _onNewMessage = async (
+  props: OnNewMessageProps
+): Promise<{ message_count: number; participant_count: number }> => {
   const message_count = props.conversation.tags.message_count ? parseInt(props.conversation.tags.message_count) + 1 : 1
 
   const participant_count = await props.client
@@ -46,29 +42,28 @@ const _onNewMessage = async (props: OnNewMessageProps) => {
   const tags = {
     message_count: message_count.toString(),
     participant_count: participant_count.toString(),
-    isDirty: props.isDirty ? 'true' : 'false',
   }
 
   await props.client.updateConversation({
     id: props.conversation.id,
     tags,
   })
+  return { message_count, participant_count }
 }
 
-type UpdateTitleAndSummaryProps = CommonProps & {
-  conversationId: string
-  messages: string[]
-}
-const _updateTitleAndSummary = async (props: UpdateTitleAndSummaryProps) => {
-  await props.client.updateConversation({
-    id: props.conversationId,
-    tags: {
-      // TODO: use the cognitive client / service to generate a title and summary
-      title: 'The conversation title!',
-      summary: 'This is normally where the conversation summary would be.',
-      isDirty: 'false',
-    },
+plugin.on.event('updateSummary', async (props) => {
+  const messages = await props.client.listMessages({ conversationId: props.event.conversationId })
+  const newMessages: string[] = messages.messages.map((message) => message.payload.text)
+  if (!props.event.conversationId) {
+    throw new sdk.RuntimeError(`The conversationId cannot be null when calling the event '${props.event.type}'`)
+  }
+  const conversation = await props.client.getConversation({ id: props.event.conversationId })
+
+  await summaryUpdater.updateTitleAndSummary({
+    ...props,
+    conversation: conversation.conversation,
+    messages: newMessages,
   })
-}
+})
 
 export default plugin
diff --git a/plugins/conversation-insights/src/summary-prompt.ts b/plugins/conversation-insights/src/summary-prompt.ts
new file mode 100644
index 00000000000..2f60caa3c02
--- /dev/null
+++ b/plugins/conversation-insights/src/summary-prompt.ts
@@ -0,0 +1,93 @@
+import { z } from '@botpress/sdk'
+import { LLMInput } from './generate-content'
+
+export type OutputFormat = z.infer<typeof OutputFormat>
+export const OutputFormat = z.object({
+  title: z.string().describe('A fitting title for the conversation'),
+  summary: z.string().describe('A short summary of the conversation'),
+})
+
+export type InputFormat = z.infer<typeof InputFormat>
+export const InputFormat = z.array(z.string())
+
+const formatMessages = (
+  messages: string[],
+  context: PromptArgs['context']
+): { role: 'user' | 'assistant'; content: string } => {
+  return {
+    role: 'user',
+    content: JSON.stringify(
+      {
+        previousTitle: context.previousTitle,
+        previousSummary: context.previousSummary,
+        messages: messages.reverse(),
+      },
+      null,
+      2
+    ),
+  }
+}
+
+export type PromptArgs = {
+  messages: string[]
+  model: { id: string }
+  context: { previousSummary?: string; previousTitle?: string }
+}
+export const createPrompt = (args: PromptArgs): LLMInput => ({
+  responseFormat: 'json_object',
+  temperature: 0,
+  systemPrompt: `
+You are a conversation summarizer.
+You will be given:
+- A previous title and summary
+- An array of USER MESSAGES
+
+Your task is to produce a title and summary that best describe the overall conversation.
+
+Return your response only in valid JSON using the following type:
+
+\`\`\`json
+{
+  "title": "string",   // A concise, fitting title for the conversation
+  "summary": "string"  // A short summary capturing the main topic or request
+}
+\`\`\`
+
+Instructions:
+
+- Consider the previous title when creating the new one — keep it if still relevant, or update it if needed.
+- Focus on the main subject of the conversation.
+- Make the title short and descriptive (few words).
+- Keep the summary concise (one or two sentences).
+- Do not include extra commentary, formatting, or explanation outside the JSON output.
+- The messages are in order, which means the most recent ones are at the end of the list.
+
+Example:
+
+Input:
+
+\`\`\`json
+{
+  "previousTitle": "Used cars",
+  "previousSummary": "The user is talking abous a used Toyota Matrix",
+  "messages": [
+    "What mileage should I expect from a car that was made two years ago?",
+    "What price should I expect from a car manufactured in 2011?",
+    "What should I look out for when buying a secondhand Toyota Matrix?",
+    "I am looking to buy a used car, what would you recommend?",
+  ]
+}
+\`\`\`
+
+Output:
+
+\`\`\`json
+{
+  "title": "Used cars",
+  "summary": "The user is seeking advice on purchasing a used car."
+}
+\`\`\`
+`.trim(),
+  messages: [formatMessages(args.messages, args.context)],
+  model: args.model,
+})
diff --git a/plugins/conversation-insights/src/summaryUpdateScheduler.ts b/plugins/conversation-insights/src/summaryUpdateScheduler.ts
new file mode 100644
index 00000000000..aa1a176682b
--- /dev/null
+++ b/plugins/conversation-insights/src/summaryUpdateScheduler.ts
@@ -0,0 +1,7 @@
+const INITIAL_UPDATE_COUNT = 3 //will update every message for the first INITIAL_UPDATE_COUNT messages
+const UPDATE_INTERVAL = 5 //after that, will update every UPDATE_INTERVAL messages
+
+export const isTimeToUpdate = (message_count: number): boolean => {
+  if (message_count <= INITIAL_UPDATE_COUNT) return true
+  return message_count % UPDATE_INTERVAL === 0
+}
diff --git a/plugins/conversation-insights/src/summaryUpdater.ts b/plugins/conversation-insights/src/summaryUpdater.ts
new file mode 100644
index 00000000000..84963078a19
--- /dev/null
+++ b/plugins/conversation-insights/src/summaryUpdater.ts
@@ -0,0 +1,44 @@
+import * as gen from './generate-content'
+import * as summarizer from './summary-prompt'
+import * as types from './types'
+import * as bp from '.botpress'
+
+type CommonProps = types.CommonProps
+
+type UpdateTitleAndSummaryProps = CommonProps & {
+  conversation: bp.MessageHandlerProps['conversation']
+  messages: string[]
+}
+export const updateTitleAndSummary = async (props: UpdateTitleAndSummaryProps) => {
+  const prompt = summarizer.createPrompt({
+    messages: props.messages,
+    model: { id: props.configuration.modelId },
+    context: { previousTitle: props.conversation.tags.title, previousSummary: props.conversation.tags.summary },
+  })
+
+  let attemptCount = 0
+  const maxRetries = 3
+
+  let llmOutput = await props.actions.llm.generateContent(prompt)
+  let parsed = gen.parseLLMOutput(llmOutput)
+
+  while (!parsed.success && attemptCount < maxRetries) {
+    props.logger.debug(`Attempt ${attemptCount + 1}: The LLM output did not respect the schema.`, parsed.json)
+    llmOutput = await props.actions.llm.generateContent(prompt)
+    parsed = gen.parseLLMOutput(llmOutput)
+    attemptCount++
+  }
+
+  if (!parsed.success) {
+    props.logger.debug(`The LLM output did not respect the schema after ${attemptCount} retries.`, parsed.json)
+    return
+  }
+
+  await props.client.updateConversation({
+    id: props.conversation.id,
+    tags: {
+      title: parsed.json.title,
+      summary: parsed.json.summary,
+    },
+  })
+}
diff --git a/plugins/conversation-insights/src/types.ts b/plugins/conversation-insights/src/types.ts
new file mode 100644
index 00000000000..3141bc3f4b4
--- /dev/null
+++ b/plugins/conversation-insights/src/types.ts
@@ -0,0 +1,7 @@
+import * as bp from '.botpress'
+
+// TODO: generate a type for CommonProps in the CLI / SDK
+export type CommonProps =
+  | bp.HookHandlerProps['after_incoming_message']
+  | bp.HookHandlerProps['after_outgoing_message']
+  | bp.EventHandlerProps
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 1aafe998a79..8fb193f3cc3 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -2589,6 +2589,16 @@ importers:
       '@botpress/sdk':
         specifier: workspace:*
         version: link:../../packages/sdk
+      json5:
+        specifier: ^2.2.3
+        version: 2.2.3
+      jsonrepair:
+        specifier: ^3.10.0
+        version: 3.10.0
+    devDependencies:
+      '@botpresshub/llm':
+        specifier: workspace:*
+        version: link:../../interfaces/llm
 
   plugins/file-synchronizer:
     dependencies: