diff --git a/packages/core/src/services/chains/ChainStreamConsumer/index.test.ts b/packages/core/src/services/chains/ChainStreamConsumer/index.test.ts
index 8914f97ea..678a290c4 100644
--- a/packages/core/src/services/chains/ChainStreamConsumer/index.test.ts
+++ b/packages/core/src/services/chains/ChainStreamConsumer/index.test.ts
@@ -134,7 +134,12 @@ describe('ChainStreamConsumer', () => {
         messages: [
           {
             role: MessageRole.assistant,
-            content: 'text response',
+            content: [
+              {
+                type: ContentType.text,
+                text: 'text response',
+              },
+            ],
             toolCalls: [],
           },
         ],
@@ -165,7 +170,12 @@ describe('ChainStreamConsumer', () => {
         messages: [
           {
             role: MessageRole.assistant,
-            content: '{\n  "object": "response"\n}',
+            content: [
+              {
+                type: ContentType.text,
+                text: '{\n  "object": "response"\n}',
+              },
+            ],
             toolCalls: [],
           },
         ],
@@ -250,14 +260,13 @@ describe('ChainStreamConsumer', () => {
         config: step.conversation.config,
         response: response,
         messages: [
-          {
-            role: MessageRole.assistant,
-            content: 'text response',
-            toolCalls: [],
-          },
           {
             role: MessageRole.assistant,
             content: [
+              {
+                type: ContentType.text,
+                text: 'text response',
+              },
               {
                 type: ContentType.toolCall,
                 toolCallId: 'tool-call-id',
diff --git a/packages/core/src/services/chains/ChainStreamConsumer/index.ts b/packages/core/src/services/chains/ChainStreamConsumer/index.ts
index 471d73d31..17329fba9 100644
--- a/packages/core/src/services/chains/ChainStreamConsumer/index.ts
+++ b/packages/core/src/services/chains/ChainStreamConsumer/index.ts
@@ -1,5 +1,6 @@
 import {
   ContentType,
+  MessageContent,
   MessageRole,
   ToolRequestContent,
 } from '@latitude-data/compiler'
@@ -56,36 +57,58 @@ export class ChainStreamConsumer {
     config: Config
   }) {
     let messages: Message[] = []
+    let message: Message | undefined = undefined
 
     if (response.text.length > 0) {
-      messages.push({
+      message = {
         role: MessageRole.assistant,
-        content: response.text,
+        content: [
+          {
+            type: ContentType.text,
+            text: response.text,
+          },
+        ],
         toolCalls: [],
-      })
+      }
     }
 
     if (response.streamType === 'object' && response.object) {
-      messages.push({
+      message = {
         role: MessageRole.assistant,
-        content: objectToString(response.object),
+        content: [
+          {
+            type: ContentType.text,
+            text: objectToString(response.object),
+          },
+        ],
         toolCalls: [],
-      })
+      }
     }
 
     if (response.streamType === 'text' && response.toolCalls.length > 0) {
-      messages.push({
-        role: MessageRole.assistant,
-        content: response.toolCalls.map((toolCall) => {
-          return {
-            type: ContentType.toolCall,
-            toolCallId: toolCall.id,
-            toolName: toolCall.name,
-            args: toolCall.arguments,
-          } as ToolRequestContent
-        }),
-        toolCalls: response.toolCalls,
+      const content = response.toolCalls.map((toolCall) => {
+        return {
+          type: ContentType.toolCall,
+          toolCallId: toolCall.id,
+          toolName: toolCall.name,
+          args: toolCall.arguments,
+        } as ToolRequestContent
       })
+
+      if (message) {
+        message.content = (message.content as MessageContent[]).concat(content)
+        message.toolCalls = response.toolCalls
+      } else {
+        message = {
+          role: MessageRole.assistant,
+          content: content,
+          toolCalls: response.toolCalls,
+        }
+      }
+    }
+
+    if (message) {
+      messages.push(message)
     }
 
     enqueueChainEvent(controller, {
diff --git a/packages/core/src/services/chains/run.test.ts b/packages/core/src/services/chains/run.test.ts
index 1151c838b..d9bf58e9f 100644
--- a/packages/core/src/services/chains/run.test.ts
+++ b/packages/core/src/services/chains/run.test.ts
@@ -662,14 +662,13 @@ describe('runChain', () => {
       data: expect.objectContaining({
         type: ChainEventTypes.Complete,
         messages: [
-          {
-            role: MessageRole.assistant,
-            content: 'assistant message',
-            toolCalls: [],
-          },
           {
             role: MessageRole.assistant,
             content: [
+              {
+                type: ContentType.text,
+                text: 'assistant message',
+              },
               {
                 type: ContentType.toolCall,
                 toolCallId: 'tool-call-id',
diff --git a/packages/core/src/services/commits/runDocumentAtCommit.test.ts b/packages/core/src/services/commits/runDocumentAtCommit.test.ts
index c204195d7..e09f7b797 100644
--- a/packages/core/src/services/commits/runDocumentAtCommit.test.ts
+++ b/packages/core/src/services/commits/runDocumentAtCommit.test.ts
@@ -263,7 +263,12 @@ model: gpt-4o
             messages: [
               {
                 role: 'assistant',
-                content: [{ type: 'text', text: 'Fake AI generated text' }],
+                content: [
+                  {
+                    type: 'text',
+                    text: 'Fake AI generated text',
+                  },
+                ],
               },
               {
                 role: 'system',
@@ -306,7 +311,12 @@ model: gpt-4o
             messages: [
               {
                 role: 'assistant',
-                content: 'Fake AI generated text',
+                content: [
+                  {
+                    type: 'text',
+                    text: 'Fake AI generated text',
+                  },
+                ],
                 toolCalls: [],
               },
             ],
diff --git a/packages/core/src/services/documentLogs/addMessages/index.test.ts b/packages/core/src/services/documentLogs/addMessages/index.test.ts
index 46d1d2a4a..657b93be7 100644
--- a/packages/core/src/services/documentLogs/addMessages/index.test.ts
+++ b/packages/core/src/services/documentLogs/addMessages/index.test.ts
@@ -6,6 +6,7 @@ import {
   LatitudeErrorCodes,
   RunErrorCodes,
 } from '@latitude-data/constants/errors'
+import { eq } from 'drizzle-orm'
 import {
   ChainEventTypes,
   Commit,
@@ -18,8 +19,10 @@ import {
   User,
   Workspace,
 } from '../../../browser'
+import { database } from '../../../client'
 import { Result, TypedResult } from '../../../lib'
 import { ProviderLogsRepository } from '../../../repositories'
+import { providerLogs } from '../../../schema'
 import { createDocumentLog, createProject } from '../../../tests/factories'
 import { testConsumeStream } from '../../../tests/helpers'
 import * as aiModule from '../../ai'
@@ -143,7 +146,18 @@ describe('addMessages', () => {
     expect(result.error).toBeDefined()
   })
 
-  it('pass arguments to AI service', async () => {
+  it('pass arguments to AI service with text response', async () => {
+    providerLog = await database
+      .update(providerLogs)
+      .set({
+        responseText: 'assistant message',
+        responseObject: null,
+        toolCalls: [],
+      })
+      .where(eq(providerLogs.id, providerLog.id))
+      .returning()
+      .then((p) => p[0]!)
+
     const { stream } = await addMessages({
       workspace,
       documentLogUuid: providerLog.documentLogUuid!,
@@ -153,7 +167,7 @@ describe('addMessages', () => {
           content: [
             {
               type: ContentType.text,
-              text: 'This is a user message',
+              text: 'user message',
             },
           ],
         },
@@ -169,7 +183,12 @@ describe('addMessages', () => {
           ...providerLog.messages,
           {
             role: MessageRole.assistant,
-            content: providerLog.responseText,
+            content: [
+              {
+                type: ContentType.text,
+                text: providerLog.responseText,
+              },
+            ],
             toolCalls: [],
           },
           {
@@ -177,7 +196,219 @@ describe('addMessages', () => {
             content: [
               {
                 type: ContentType.text,
-                text: 'This is a user message',
+                text: 'user message',
+              },
+            ],
+          },
+        ]),
+        config: expect.objectContaining({
+          model: 'gpt-4o',
+          provider: 'openai',
+        }),
+        provider: expect.any(Object),
+      }),
+    )
+  })
+
+  it('pass arguments to AI service with object response', async () => {
+    providerLog = await database
+      .update(providerLogs)
+      .set({
+        responseText: null,
+        responseObject: { object: 'response' },
+        toolCalls: [],
+      })
+      .where(eq(providerLogs.id, providerLog.id))
+      .returning()
+      .then((p) => p[0]!)
+
+    const { stream } = await addMessages({
+      workspace,
+      documentLogUuid: providerLog.documentLogUuid!,
+      messages: [
+        {
+          role: MessageRole.user,
+          content: [
+            {
+              type: ContentType.text,
+              text: 'user message',
+            },
+          ],
+        },
+      ],
+      source: LogSources.API,
+    }).then((r) => r.unwrap())
+
+    await testConsumeStream(stream)
+
+    expect(mocks.ai).toHaveBeenCalledWith(
+      expect.objectContaining({
+        messages: expect.arrayContaining([
+          ...providerLog.messages,
+          {
+            role: MessageRole.assistant,
+            content: [
+              {
+                type: ContentType.text,
+                text: '{\n  "object": "response"\n}',
+              },
+            ],
+            toolCalls: [],
+          },
+          {
+            role: MessageRole.user,
+            content: [
+              {
+                type: ContentType.text,
+                text: 'user message',
+              },
+            ],
+          },
+        ]),
+        config: expect.objectContaining({
+          model: 'gpt-4o',
+          provider: 'openai',
+        }),
+        provider: expect.any(Object),
+      }),
+    )
+  })
+
+  it('pass arguments to AI service with tool calls response', async () => {
+    providerLog = await database
+      .update(providerLogs)
+      .set({
+        responseText: null,
+        responseObject: null,
+        toolCalls: [
+          {
+            id: 'tool-call-id',
+            name: 'tool-call-name',
+            arguments: { arg1: 'value1', arg2: 'value2' },
+          },
+        ],
+      })
+      .where(eq(providerLogs.id, providerLog.id))
+      .returning()
+      .then((p) => p[0]!)
+
+    const { stream } = await addMessages({
+      workspace,
+      documentLogUuid: providerLog.documentLogUuid!,
+      messages: [
+        {
+          role: MessageRole.user,
+          content: [
+            {
+              type: ContentType.text,
+              text: 'user message',
+            },
+          ],
+        },
+      ],
+      source: LogSources.API,
+    }).then((r) => r.unwrap())
+
+    await testConsumeStream(stream)
+
+    expect(mocks.ai).toHaveBeenCalledWith(
+      expect.objectContaining({
+        messages: expect.arrayContaining([
+          ...providerLog.messages,
+          {
+            role: MessageRole.assistant,
+            content: [
+              {
+                type: ContentType.toolCall,
+                toolCallId: 'tool-call-id',
+                toolName: 'tool-call-name',
+                args: { arg1: 'value1', arg2: 'value2' },
+              },
+            ],
+            toolCalls: providerLog.toolCalls,
+          },
+          {
+            role: MessageRole.user,
+            content: [
+              {
+                type: ContentType.text,
+                text: 'user message',
+              },
+            ],
+          },
+        ]),
+        config: expect.objectContaining({
+          model: 'gpt-4o',
+          provider: 'openai',
+        }),
+        provider: expect.any(Object),
+      }),
+    )
+  })
+
+  it('pass arguments to AI service with tool calls and text response', async () => {
+    providerLog = await database
+      .update(providerLogs)
+      .set({
+        responseText: 'assistant message',
+        responseObject: null,
+        toolCalls: [
+          {
+            id: 'tool-call-id',
+            name: 'tool-call-name',
+            arguments: { arg1: 'value1', arg2: 'value2' },
+          },
+        ],
+      })
+      .where(eq(providerLogs.id, providerLog.id))
+      .returning()
+      .then((p) => p[0]!)
+
+    const { stream } = await addMessages({
+      workspace,
+      documentLogUuid: providerLog.documentLogUuid!,
+      messages: [
+        {
+          role: MessageRole.user,
+          content: [
+            {
+              type: ContentType.text,
+              text: 'user message',
+            },
+          ],
+        },
+      ],
+      source: LogSources.API,
+    }).then((r) => r.unwrap())
+
+    await testConsumeStream(stream)
+
+    expect(mocks.ai).toHaveBeenCalledWith(
+      expect.objectContaining({
+        messages: expect.arrayContaining([
+          ...providerLog.messages,
+          {
+            role: MessageRole.assistant,
+            content: [
+              {
+                type: ContentType.text,
+                text: providerLog.responseText,
+              },
+              {
+                type: ContentType.toolCall,
+                toolCallId: 'tool-call-id',
+                toolName: 'tool-call-name',
+                args: { arg1: 'value1', arg2: 'value2' },
+              },
+            ],
+            toolCalls: providerLog.toolCalls,
+          },
+          {
+            role: MessageRole.user,
+            content: [
+              {
+                type: ContentType.text,
+                text: 'user message',
               },
             ],
           },
@@ -234,7 +465,12 @@ describe('addMessages', () => {
           messages: [
             {
               role: 'assistant',
-              content: 'Fake AI generated text',
+              content: [
+                {
+                  type: ContentType.text,
+                  text: 'Fake AI generated text',
+                },
+              ],
               toolCalls: [],
             },
           ],
@@ -405,14 +641,13 @@ describe('addMessages', () => {
         data: expect.objectContaining({
           type: ChainEventTypes.Complete,
           messages: [
-            {
-              role: MessageRole.assistant,
-              content: 'assistant message',
-              toolCalls: [],
-            },
             {
               role: MessageRole.assistant,
               content: [
+                {
+                  type: ContentType.text,
+                  text: 'assistant message',
+                },
                 {
                   type: ContentType.toolCall,
                   toolCallId: 'tool-call-id',
diff --git a/packages/core/src/services/providerLogs/addMessages.ts b/packages/core/src/services/providerLogs/addMessages.ts
index 11f64bb6d..cee1d7d0f 100644
--- a/packages/core/src/services/providerLogs/addMessages.ts
+++ b/packages/core/src/services/providerLogs/addMessages.ts
@@ -1,6 +1,7 @@
 import {
   ContentType,
   Message,
+  MessageContent,
   MessageRole,
   ToolRequestContent,
 } from '@latitude-data/compiler'
@@ -31,37 +32,59 @@ import {
 } from '../chains/ProviderProcessor/saveOrPublishProviderLogs'
 
 function rebuildConversation(providerLog: ProviderLog) {
-  let messages = providerLog.messages
+  let messages: Message[] = providerLog.messages
+  let message: Message | undefined = undefined
 
   if (providerLog.responseText && providerLog.responseText.length > 0) {
-    messages.push({
+    message = {
       role: MessageRole.assistant,
-      content: providerLog.responseText,
+      content: [
+        {
+          type: ContentType.text,
+          text: providerLog.responseText,
+        },
+      ],
       toolCalls: [],
-    })
+    }
   }
 
   if (providerLog.responseObject) {
-    messages.push({
+    message = {
       role: MessageRole.assistant,
-      content: objectToString(providerLog.responseObject),
+      content: [
+        {
+          type: ContentType.text,
+          text: objectToString(providerLog.responseObject),
+        },
+      ],
       toolCalls: [],
-    })
+    }
   }
 
   if (providerLog.toolCalls.length > 0) {
-    messages.push({
-      role: MessageRole.assistant,
-      content: providerLog.toolCalls.map((toolCall) => {
-        return {
-          type: ContentType.toolCall,
-          toolCallId: toolCall.id,
-          toolName: toolCall.name,
-          args: toolCall.arguments,
-        } as ToolRequestContent
-      }),
-      toolCalls: providerLog.toolCalls,
+    const content = providerLog.toolCalls.map((toolCall) => {
+      return {
+        type: ContentType.toolCall,
+        toolCallId: toolCall.id,
+        toolName: toolCall.name,
+        args: toolCall.arguments,
+      } as ToolRequestContent
     })
+
+    if (message) {
+      message.content = (message.content as MessageContent[]).concat(content)
+      message.toolCalls = providerLog.toolCalls
+    } else {
+      message = {
+        role: MessageRole.assistant,
+        content: content,
+        toolCalls: providerLog.toolCalls,
+      }
+    }
+  }
+
+  if (message) {
+    messages.push(message)
   }
 
   return messages