diff --git a/packages/dd-trace/src/llmobs/plugins/ai/util.js b/packages/dd-trace/src/llmobs/plugins/ai/util.js
index 0909431e9a..8b629dab50 100644
--- a/packages/dd-trace/src/llmobs/plugins/ai/util.js
+++ b/packages/dd-trace/src/llmobs/plugins/ai/util.js
@@ -13,6 +13,8 @@ const MODEL_METADATA_KEYS = new Set([
 const VERCEL_AI_TELEMETRY_METADATA_PREFIX = 'ai.telemetry.metadata.'
 const VERCEL_AI_MODEL_METADATA_PREFIX = 'gen_ai.request.'
 const VERCEL_AI_GENERATION_METADATA_PREFIX = 'ai.settings.'
+const UNPARSABLE_TOOL_RESULT = '[Unparsable Tool Result]'
+const UNSUPPORTED_TOOL_RESULT = '[Unsupported Tool Result]'
 
 /**
  * @typedef {import('../../../opentracing/span')} Span
@@ -26,8 +28,31 @@ const VERCEL_AI_GENERATION_METADATA_PREFIX = 'ai.settings.'
 
 /**
  * @typedef {{
- *   type: string,
- *   value?: unknown
+ *   type: 'text',
+ *   text: string
+ * } | {
+ *   type: 'media' | 'file',
+ *   mediaType: string
+ * } | {
+ *   type: 'file-data' | 'file-url' | 'file-id' | 'file-reference'
+ * } | {
+ *   type: 'image-data' | 'image-url' | 'image-file-id' | 'image-file-reference'
+ * } | {
+ *   type: 'custom'
+ * }} ToolCallContentPart
+ *
+ * @typedef {{
+ *   type: 'text' | 'error-text',
+ *   value: string
+ * } | {
+ *   type: 'json' | 'error-json',
+ *   value: unknown
+ * } | {
+ *   type: 'content',
+ *   value: ToolCallContentPart[]
+ * } | {
+ *   type: 'execution-denied',
+ *   reason?: string
  * }} ToolCallOutput
  *
  * @typedef {{ output?: ToolCallOutput, result?: unknown } & Record<string, unknown>} ToolCallResultContent
@@ -304,32 +329,89 @@ function getToolNameFromTags (tags) {
 }
 
 /**
- * Get the content of a tool call result.
- * Version 5 of the ai sdk sets this tag as `content.output`, with a `
- * @param {{ output?: { type: string, value: unknown }, result?: unknown }} content
+ * @param {unknown} value
+ * @returns {string}
+ */
+function stringifyToolCallResult (value) {
+  return JSON.stringify(value) ?? UNPARSABLE_TOOL_RESULT
+}
+
+/**
+ * @param {ToolCallContentPart[]} value
+ * @returns {string}
+ */
+function formatToolCallContent (value) {
+  if (!Array.isArray(value)) return UNPARSABLE_TOOL_RESULT
+
+  let result = ''
+  for (const part of value) {
+    if (typeof part !== 'object' || part === null) return UNPARSABLE_TOOL_RESULT
+
+    const { type } = part
+    if (type === 'text') {
+      if (typeof part.text !== 'string') return UNPARSABLE_TOOL_RESULT
+      result += part.text
+    } else if (type === 'media' || type === 'file') {
+      const { mediaType } = part
+      if (typeof mediaType !== 'string') return UNPARSABLE_TOOL_RESULT
+      result += mediaType === 'image' || mediaType.startsWith('image/') ? '[Image]' : '[File]'
+    } else if (
+      type === 'file-data' ||
+      type === 'file-url' ||
+      type === 'file-id' ||
+      type === 'file-reference'
+    ) {
+      result += '[File]'
+    } else if (
+      type === 'image-data' ||
+      type === 'image-url' ||
+      type === 'image-file-id' ||
+      type === 'image-file-reference'
+    ) {
+      result += '[Image]'
+    } else if (type === 'custom') {
+      result += '[Custom Content]'
+    } else {
+      return UNPARSABLE_TOOL_RESULT
+    }
+  }
+
+  return result
+}
+
+/**
+ * @param {ToolCallResultContent | null | undefined} content
  * @returns {string}
  */
 function getToolCallResultContent (content) {
-  const { output, result } = content
-  if (output) {
-    if (output.type === 'text') {
-      return output.value
-    } else if (output.type === 'json') {
-      return JSON.stringify(output.value)
+  try {
+    if (typeof content !== 'object' || content === null) return UNPARSABLE_TOOL_RESULT
+
+    const { output, result } = content
+    if (output !== undefined) {
+      if (typeof output !== 'object' || output === null) return UNPARSABLE_TOOL_RESULT
+
+      const { type, value } = output
+      if (type === 'text' || type === 'error-text') {
+        return typeof value === 'string' ? value : UNPARSABLE_TOOL_RESULT
+      } else if (type === 'json' || type === 'error-json') {
+        return stringifyToolCallResult(value)
+      } else if (type === 'content') {
+        return formatToolCallContent(value)
+      } else if (type === 'execution-denied') {
+        const { reason } = output
+        if (reason === undefined) return '[Tool Execution Denied]'
+        return typeof reason === 'string' ? reason : UNPARSABLE_TOOL_RESULT
+      }
+      return UNPARSABLE_TOOL_RESULT
     }
-    return '[Unparsable Tool Result]'
-  } else if (result) {
-    if (typeof result === 'string') {
-      return result
+    if (result !== undefined) {
+      return typeof result === 'string' ? result : stringifyToolCallResult(result)
     }
 
-    try {
-      return JSON.stringify(result)
-    } catch {
-      return '[Unparsable Tool Result]'
-    }
-  } else {
-    return '[Unsupported Tool Result]'
+    return UNSUPPORTED_TOOL_RESULT
+  } catch {
+    return UNPARSABLE_TOOL_RESULT
   }
 }
 
diff --git a/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0361f19b.json b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0361f19b.json
new file mode 100644
index 0000000000..d34da23252
--- /dev/null
+++ b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0361f19b.json
@@ -0,0 +1,50 @@
+{
+  "request": {
+    "method": "POST",
+    "url": "https://api.openai.com/v1/chat/completions",
+    "headers": {
+      "Connection": "keep-alive",
+      "Content-Type": "application/json",
+      "User-Agent": "ai/5.0.218 ai-sdk/provider-utils/3.0.30 runtime/node.js/24",
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+  },
+  "response": {
+    "status": {
+      "code": 200,
+      "message": "OK"
+    },
+    "headers": {
+      "Date": "Wed, 22 Jul 2026 20:13:31 GMT",
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+      "x-ratelimit-remaining-tokens": "149999985",
+      "x-ratelimit-reset-requests": "2ms",
+      "x-ratelimit-reset-tokens": "0s",
+      "x-request-id": "req_6e1a2998fd994324bdc2bd3ae10e3b19",
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+      "Content-Encoding": "gzip",
+      "alt-svc": "h3=\":443\"; ma=86400"
+    },
+    "body": "{\n  \"id\": \"chatcmpl-E4XbmnhhTOv8VuwXC9YKsgbUKoh53\",\n  \"object\": \"chat.completion\",\n  \"created\": 1784751210,\n  \"model\": \"gpt-4o-mini-2024-07-18\",\n  \"choices\": [\n    {\n      \"index\": 0,\n      \"message\": {\n        \"role\": \"assistant\",\n        \"content\": \"It seems there was an error when trying to run the test tool. The tool returned a failure message. Let me know if there's anything else you'd like to do or explore!\",\n        \"refusal\": null,\n        \"annotations\": []\n      },\n      \"logprobs\": null,\n      \"finish_reason\": \"stop\"\n    }\n  ],\n  \"usage\": {\n    \"prompt_tokens\": 68,\n    \"completion_tokens\": 36,\n    \"total_tokens\": 104,\n    \"prompt_tokens_details\": {\n      \"cached_tokens\": 0,\n      \"audio_tokens\": 0\n    },\n    \"completion_tokens_details\": {\n      \"reasoning_tokens\": 0,\n      \"audio_tokens\": 0,\n      \"accepted_prediction_tokens\": 0,\n      \"rejected_prediction_tokens\": 0\n    }\n  },\n  \"service_tier\": \"default\",\n  \"system_fingerprint\": \"fp_67faaa3b02\"\n}\n"
+  }
+}
\ No newline at end of file
diff --git a/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0529368f.json b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0529368f.json
new file mode 100644
index 0000000000..aa06581a43
--- /dev/null
+++ b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0529368f.json
@@ -0,0 +1,50 @@
+{
+  "request": {
+    "method": "POST",
+    "url": "https://api.openai.com/v1/chat/completions",
+    "headers": {
+      "Connection": "keep-alive",
+      "Content-Type": "application/json",
+      "User-Agent": "ai/7.0.31 ai-sdk/provider-utils/5.0.0 runtime/node.js/24",
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+      "Accept-Language": "*",
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+  },
+  "response": {
+    "status": {
+      "code": 200,
+      "message": "OK"
+    },
+    "headers": {
+      "Date": "Wed, 22 Jul 2026 20:14:35 GMT",
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+      "x-ratelimit-reset-requests": "2ms",
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+      "Content-Encoding": "gzip",
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+  }
+}
\ No newline at end of file
diff --git a/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_09caa127.json b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_09caa127.json
new file mode 100644
index 0000000000..3ae952aacc
--- /dev/null
+++ b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_09caa127.json
@@ -0,0 +1,50 @@
+{
+  "request": {
+    "method": "POST",
+    "url": "https://api.openai.com/v1/chat/completions",
+    "headers": {
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+  },
+  "response": {
+    "status": {
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+      "message": "OK"
+    },
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+  }
+}
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diff --git a/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0b6f9297.json b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0b6f9297.json
new file mode 100644
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+++ b/packages/dd-trace/test/llmobs/cassettes/openai/openai_chat_completions_post_0b6f9297.json
@@ -0,0 +1,50 @@
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--- a/packages/dd-trace/test/llmobs/plugins/ai/index.spec.js
+++ b/packages/dd-trace/test/llmobs/plugins/ai/index.spec.js
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 const { useEnv } = require('../../../../../../integration-tests/helpers')
 const { withVersions } = require('../../../setup/mocha')
 const iastFilter = require('../../../../src/appsec/iast/taint-tracking/filter')
+const { getToolCallResultContent } = require('../../../../src/llmobs/plugins/ai/util')
 
 const { NODE_MAJOR } = require('../../../../../../version')
 
@@ -19,6 +20,9 @@ const {
   MOCK_OBJECT,
 } = require('../../util')
 
+const UNPARSABLE_TOOL_RESULT = '[Unparsable Tool Result]'
+const UNSUPPORTED_TOOL_RESULT = '[Unsupported Tool Result]'
+
 // ai<4.0.2 is not supported in CommonJS with Node.js < 22
 const range = NODE_MAJOR < 22 ? '>=4.0.2 <7.0.0' : '>=4.0.0 <7.0.0'
 
@@ -63,12 +67,17 @@ function getAiSdkAnthropicOrGoogleRange (vercelAiVersion) {
 
 /**
  * @param {string} versionRange
- * @param {(version: string, realVersion: string, openaiVersion: string) => void} callback
+ * @param {(
+ *   version: string,
+ *   realVersion: string,
+ *   openaiVersionKey: string,
+ *   openaiVersion: string
+ * ) => void} callback
  */
 function withAiSdkOpenAiVersions (versionRange, callback) {
   withVersions('ai', 'ai', versionRange, (version, _, realVersion) => {
-    withVersions('ai', '@ai-sdk/openai', getAiSdkOpenAiRange(realVersion), openaiVersion => {
-      callback(version, realVersion, openaiVersion)
+    withVersions('ai', '@ai-sdk/openai', getAiSdkOpenAiRange(realVersion), (openaiVersionKey, _, openaiVersion) => {
+      callback(version, realVersion, openaiVersionKey, openaiVersion)
     })
   })
 }
@@ -79,6 +88,109 @@ const MOCK_TELEMETRY_METADATA = {
   conversationId: 'convAbc123',
 }
 
+const TOOL_RESULT_SCENARIOS = [
+  {
+    name: 'multipart content',
+    execute: () => 'result',
+    createModelOutput: () => ({
+      type: 'content',
+      value: [
+        { type: 'text', text: 'before' },
+        { type: 'media', mediaType: 'image/png', data: 'private-image-data' },
+        { type: 'media', mediaType: 'application/pdf', data: 'private-file-data' },
+        { type: 'file-data', mediaType: 'application/pdf', data: 'private-file-data' },
+        { type: 'file-id', fileId: 'private-file-id' },
+        { type: 'image-data', mediaType: 'image/png', data: 'private-image-data' },
+        { type: 'image-file-id', fileId: 'private-image-id' },
+        { type: 'custom', providerOptions: { secret: 'provider-data' } },
+        { type: 'text', text: 'after' },
+      ],
+    }),
+    expectedContent: 'before[Image][File][File][File][Image][Image][Custom Content]after',
+  },
+  {
+    name: 'text',
+    execute: () => 'result',
+    expectedContent: 'result',
+  },
+  {
+    name: 'JSON',
+    execute: () => ({ answer: 42 }),
+    expectedContent: '{"answer":42}',
+  },
+  {
+    name: 'error text',
+    execute: () => {
+      throw new Error('tool failure')
+    },
+    expectedContent: 'tool failure',
+  },
+  {
+    name: 'error JSON',
+    execute: () => 'result',
+    createModelOutput: () => ({
+      type: 'error-json',
+      value: { message: 'tool failure' },
+    }),
+    expectedContent: '{"message":"tool failure"}',
+  },
+  {
+    name: 'empty multipart content',
+    execute: () => 'result',
+    createModelOutput: () => ({ type: 'content', value: [] }),
+    expectedContent: '',
+  },
+  {
+    name: 'denied execution',
+    openaiRange: '>=3.0.0',
+    execute: () => 'result',
+    createModelOutput: () => ({
+      type: 'execution-denied',
+      reason: 'Approval rejected',
+    }),
+    expectedContent: 'Approval rejected',
+  },
+  {
+    name: 'denied execution without a reason',
+    openaiRange: '>=3.0.0',
+    execute: () => 'result',
+    createModelOutput: () => ({ type: 'execution-denied' }),
+    expectedContent: '[Tool Execution Denied]',
+  },
+  {
+    name: 'malformed multipart content',
+    execute: () => 'result',
+    createModelOutput: () => ({
+      type: 'content',
+      value: [{ type: 'unknown' }],
+    }),
+    expectedContent: UNPARSABLE_TOOL_RESULT,
+  },
+]
+
+const LEGACY_TOOL_RESULT_SCENARIOS = [
+  {
+    name: 'empty legacy result',
+    execute: () => '',
+    expectedContent: '',
+  },
+  {
+    name: 'zero legacy result',
+    execute: () => 0,
+    expectedContent: '0',
+  },
+  {
+    name: 'false legacy result',
+    execute: () => false,
+    expectedContent: 'false',
+  },
+  {
+    name: 'null legacy result',
+    execute: () => null,
+    expectedContent: 'null',
+  },
+]
+
 describe('Plugin', () => {
   useEnv({
     OPENAI_API_KEY: '<not-a-real-key>',
@@ -1159,6 +1271,192 @@ describe('Plugin', () => {
     })
   })
 
+  describe('tool result formatting', () => {
+    withAiSdkOpenAiVersions(range, (version, realVersion, openaiVersionKey, openaiVersion) => {
+      let ai
+      let openai
+
+      beforeEach(() => {
+        ai = require(`../../../../../../versions/ai@${version}`).get()
+
+        const OpenAIModule = require(`../../../../../../versions/@ai-sdk/openai@${openaiVersionKey}`)
+        const OpenAI = OpenAIModule.get()
+        openai = OpenAI.createOpenAI({
+          baseURL: 'http://127.0.0.1:9126/vcr/openai',
+          compatibility: 'strict',
+        })
+      })
+
+      /**
+       * @param {{
+       *   execute: () => unknown,
+       *   createModelOutput?: () => unknown,
+       *   expectedContent: string,
+       *   openaiRange?: string
+       * }} scenario
+       */
+      async function assertToolResult (scenario) {
+        const isLegacy = semifies(realVersion, '<5.0.0')
+        const schema = ai.jsonSchema({
+          type: 'object',
+          properties: {},
+        })
+        let tool
+        if (isLegacy) {
+          tool = ai.tool({
+            id: 'testTool',
+            description: 'Run the test tool and return its result',
+            parameters: schema,
+            execute: scenario.execute,
+          })
+        } else {
+          tool = ai.tool({
+            description: 'Run the test tool and return its result',
+            inputSchema: schema,
+            execute: scenario.execute,
+            toModelOutput: scenario.createModelOutput,
+          })
+        }
+
+        const options = {
+          // Chat Completions serializes every tool result as text. The Responses API rejects some valid AI SDK
+          // result variants before the instrumented request can capture their formatted value.
+          model: openai.chat('gpt-4o-mini'),
+          prompt: 'Run the test tool',
+          tools: isLegacy ? [tool] : { testTool: tool },
+        }
+        if (isLegacy) {
+          options.maxSteps = 2
+        } else {
+          options.stopWhen = ai.stepCountIs(2)
+        }
+        if (semifies(openaiVersion, '>=2.0.50')) {
+          options.providerOptions = {
+            openai: {
+              store: false,
+            },
+          }
+        }
+
+        const result = await ai.generateText(options)
+        const toolCallId = result.steps[0].toolCalls[0].toolCallId
+
+        const { apmSpans, llmobsSpans } = await getEvents(4)
+        let finalModelSpan
+        let finalModelApmSpan
+        let workflowSpan
+        for (const span of llmobsSpans) {
+          if (span.name === 'doGenerate') {
+            finalModelSpan = span
+          } else if (span.name === 'generateText') {
+            workflowSpan = span
+          }
+        }
+        for (const span of apmSpans) {
+          if (span.name === 'ai.generateText.doGenerate') finalModelApmSpan = span
+        }
+
+        assertLlmObsSpanEvent(finalModelSpan, {
+          span: finalModelApmSpan,
+          parentId: workflowSpan.span_id,
+          spanKind: 'llm',
+          modelName: 'gpt-4o-mini',
+          modelProvider: 'openai',
+          name: 'doGenerate',
+          inputMessages: [
+            { content: 'Run the test tool', role: 'user' },
+            {
+              content: '',
+              role: 'assistant',
+              tool_calls: [{
+                tool_id: toolCallId,
+                name: 'testTool',
+                arguments: {},
+                type: 'function',
+              }],
+            },
+            {
+              content: scenario.expectedContent,
+              role: 'tool',
+              tool_id: toolCallId,
+            },
+          ],
+          outputMessages: [MOCK_OBJECT],
+          metrics: { input_tokens: MOCK_NUMBER, output_tokens: MOCK_NUMBER, total_tokens: MOCK_NUMBER },
+          tags: { ml_app: 'test', integration: 'ai' },
+        })
+      }
+
+      const scenarios = semifies(realVersion, '<5.0.0')
+        ? LEGACY_TOOL_RESULT_SCENARIOS
+        : TOOL_RESULT_SCENARIOS.filter(({ openaiRange }) => !openaiRange || semifies(openaiVersion, openaiRange))
+      for (const scenario of scenarios) {
+        it(`formats ${scenario.name} produced by the AI SDK`, async () => {
+          await assertToolResult(scenario)
+        })
+      }
+    })
+
+    it('falls back for values rejected before model invocation', () => {
+      const circular = {}
+      circular.self = circular
+
+      const malformedOutputs = [
+        null,
+        'text',
+        { type: 'text' },
+        { type: 'text', value: 42 },
+        { type: 'json', value: undefined },
+        { type: 'json', value: Symbol('result') },
+        { type: 'json', value: 1n },
+        { type: 'json', value: circular },
+        { type: 'content', value: {} },
+        { type: 'content', value: [null] },
+        { type: 'content', value: [{ type: 'text' }] },
+        { type: 'content', value: [{ type: 'media' }] },
+        { type: 'execution-denied', reason: {} },
+        { type: 'unknown', value: 'result' },
+      ]
+
+      for (const output of malformedOutputs) {
+        assert.strictEqual(
+          getToolCallResultContent({ output }),
+          UNPARSABLE_TOOL_RESULT
+        )
+      }
+
+      assert.strictEqual(getToolCallResultContent(), UNPARSABLE_TOOL_RESULT)
+      assert.strictEqual(getToolCallResultContent(null), UNPARSABLE_TOOL_RESULT)
+      assert.strictEqual(getToolCallResultContent('result'), UNPARSABLE_TOOL_RESULT)
+      assert.strictEqual(getToolCallResultContent({}), UNSUPPORTED_TOOL_RESULT)
+    })
+
+    it('does not throw for external objects rejected before model invocation', () => {
+      const throwingContent = new Proxy({}, {
+        get () {
+          throw new Error('unexpected content access')
+        },
+      })
+      const throwingOutput = new Proxy({}, {
+        get () {
+          throw new Error('unexpected output access')
+        },
+      })
+      const throwingParts = new Proxy([], {
+        get () {
+          throw new Error('unexpected content part access')
+        },
+      })
+
+      assert.strictEqual(getToolCallResultContent(throwingContent), UNPARSABLE_TOOL_RESULT)
+      assert.strictEqual(getToolCallResultContent({ output: throwingOutput }), UNPARSABLE_TOOL_RESULT)
+      assert.strictEqual(
+        getToolCallResultContent({ output: { type: 'content', value: throwingParts } }),
+        UNPARSABLE_TOOL_RESULT
+      )
+    })
+  })
+
   describe('prompt cache token capture', () => {
     // Both @ai-sdk/amazon-bedrock and @ai-sdk/anthropic use globalThis.fetch
     // (not node:http), so nock cannot intercept them. Each provider's
diff --git a/packages/dd-trace/test/llmobs/plugins/ai/index.v7.spec.js b/packages/dd-trace/test/llmobs/plugins/ai/index.v7.spec.js
index 52a686a5c2..dd3b400ca2 100644
--- a/packages/dd-trace/test/llmobs/plugins/ai/index.v7.spec.js
+++ b/packages/dd-trace/test/llmobs/plugins/ai/index.v7.spec.js
@@ -11,6 +11,7 @@ const {
   MOCK_STRING,
   useLlmObs,
   MOCK_NUMBER,
+  MOCK_OBJECT,
 } = require('../../util')
 
 /**
@@ -946,6 +947,137 @@ describe('Plugin', () => {
     })
   })
 
+  describe('tool result formatting', () => {
+    withAiSdkOpenAiVersions((version, _, openaiVersion) => {
+      let ai
+      let openai
+
+      beforeEach(() => {
+        ai = require(`../../../../../../versions/ai@${version}`).get()
+
+        const OpenAI = require(`../../../../../../versions/@ai-sdk/openai@${openaiVersion}`).get()
+        openai = OpenAI.createOpenAI({
+          baseURL: 'http://127.0.0.1:9126/vcr/openai',
+          compatibility: 'strict',
+        })
+      })
+
+      it('formats file result parts produced by the AI SDK', async () => {
+        const result = await ai.generateText({
+          // Chat Completions serializes every tool result as text. The Responses API validates file contents before
+          // the instrumented request can capture their formatted value.
+          model: openai.chat('gpt-4o-mini'),
+          prompt: 'Run the test tool',
+          tools: {
+            testTool: ai.tool({
+              description: 'Run the test tool and return its result',
+              inputSchema: ai.jsonSchema({
+                type: 'object',
+                properties: {},
+              }),
+              execute: () => 'result',
+              toModelOutput: () => ({
+                type: 'content',
+                value: [
+                  { type: 'text', text: 'before' },
+                  {
+                    type: 'file',
+                    mediaType: 'image/png',
+                    data: { type: 'data', data: 'cHJpdmF0ZS1pbWFnZS1kYXRh' },
+                  },
+                  {
+                    type: 'file',
+                    mediaType: 'application/pdf',
+                    data: { type: 'data', data: 'cHJpdmF0ZS1maWxlLWRhdGE=' },
+                  },
+                  {
+                    type: 'file',
+                    mediaType: 'application/pdf',
+                    data: { type: 'reference', reference: { test: 'private-file-id' } },
+                  },
+                  {
+                    type: 'file',
+                    mediaType: 'image/png',
+                    data: { type: 'reference', reference: { test: 'private-image-id' } },
+                  },
+                  { type: 'custom', providerOptions: { secret: 'provider-data' } },
+                  { type: 'text', text: 'after' },
+                ],
+              }),
+            }),
+          },
+          stopWhen: ai.stepCountIs(2),
+          providerOptions: {
+            openai: {
+              store: false,
+            },
+          },
+        })
+        const toolCallId = result.steps[0].toolCalls[0].toolCallId
+
+        const { apmSpans, llmobsSpans } = await getEvents(6)
+        let finalModelSpan
+        let finalModelApmSpan
+        let finalStepSpan
+        for (const span of llmobsSpans) {
+          if (span.name === 'languageModelCall') {
+            finalModelSpan = span
+          } else if (span.name === 'step') {
+            finalStepSpan = span
+          }
+        }
+        for (const span of apmSpans) {
+          if (span.name === 'languageModelCall') finalModelApmSpan = span
+        }
+
+        assertLlmObsSpanEvent(finalModelSpan, {
+          span: finalModelApmSpan,
+          parentId: finalStepSpan.span_id,
+          spanKind: 'llm',
+          modelName: 'gpt-4o-mini',
+          modelProvider: 'openai',
+          name: 'languageModelCall',
+          inputMessages: [
+            { content: 'Run the test tool', role: 'user' },
+            {
+              role: 'assistant',
+              tool_calls: [{
+                tool_id: toolCallId,
+                name: 'testTool',
+                arguments: {},
+                type: 'function',
+              }],
+            },
+            {
+              content: 'before[Image][File][File][Image][Custom Content]after',
+              role: 'tool',
+              tool_id: toolCallId,
+            },
+          ],
+          outputMessages: [MOCK_OBJECT],
+          toolDefinitions: [{
+            name: 'testTool',
+            description: 'Run the test tool and return its result',
+            schema: {
+              type: 'object',
+              properties: {},
+              required: [],
+            },
+          }],
+          metadata: {},
+          metrics: {
+            input_tokens: MOCK_NUMBER,
+            cache_write_input_tokens: 0,
+            cache_read_input_tokens: 0,
+            output_tokens: MOCK_NUMBER,
+            reasoning_output_tokens: 0,
+          },
+          tags: { ml_app: 'test', integration: 'ai' },
+        })
+      })
+    })
+  })
+
   describe('prompt cache token capture', () => {
     function makeMockFetch (scenario) {
       const fixture = require(`../../../../../datadog-plugin-ai/test/resources/${scenario}.json`)