diff --git a/src/api/providers/__tests__/bedrock-image-limiting.spec.ts b/src/api/providers/__tests__/bedrock-image-limiting.spec.ts
new file mode 100644
index 0000000000..47fd9cc51a
--- /dev/null
+++ b/src/api/providers/__tests__/bedrock-image-limiting.spec.ts
@@ -0,0 +1,299 @@
+// npx vitest run src/api/providers/__tests__/bedrock-image-limiting.spec.ts
+
+import { describe, it, expect, vi, beforeEach } from "vitest"
+import { Anthropic } from "@anthropic-ai/sdk"
+import { AwsBedrockHandler } from "../bedrock"
+import { ApiHandlerOptions } from "../../../shared/api"
+import { AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION } from "../../transform/image-limiting"
+
+// Valid base64 encoded 1x1 pixel PNG image for testing
+const VALID_BASE64_IMAGE =
+	"iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mNkYPhfDwAChAGAWA0+kgAAAABJRU5ErkJggg=="
+
+// Mock AWS SDK
+vi.mock("@aws-sdk/client-bedrock-runtime", () => {
+	return {
+		BedrockRuntimeClient: vi.fn().mockImplementation(() => ({
+			send: vi.fn(),
+		})),
+		ConverseStreamCommand: vi.fn(),
+		ConverseCommand: vi.fn(),
+	}
+})
+
+// Mock credential providers
+vi.mock("@aws-sdk/credential-providers", () => ({
+	fromIni: vi.fn().mockReturnValue({
+		accessKeyId: "test-access-key",
+		secretAccessKey: "test-secret-key",
+	}),
+}))
+
+describe("AwsBedrockHandler - Image Limiting", () => {
+	let handler: AwsBedrockHandler
+	let mockOptions: ApiHandlerOptions
+
+	beforeEach(() => {
+		mockOptions = {
+			apiModelId: "anthropic.claude-3-5-sonnet-20241022-v2:0",
+			awsAccessKey: "test-access-key",
+			awsSecretKey: "test-secret-key",
+			awsRegion: "us-east-1",
+		}
+		handler = new AwsBedrockHandler(mockOptions)
+	})
+
+	describe("convertToBedrockConverseMessages with image limiting", () => {
+		it("should not modify messages when under image limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "Look at this image:" },
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/png", data: VALID_BASE64_IMAGE },
+						},
+					],
+				},
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "And this one:" },
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/jpeg", data: VALID_BASE64_IMAGE },
+						},
+					],
+				},
+			]
+
+			// Access the private method for testing
+			const result = (handler as any).convertToBedrockConverseMessages(messages, "System prompt")
+
+			// Should have 2 messages with images intact
+			expect(result.messages).toHaveLength(2)
+
+			// Check that images are preserved
+			const firstMessage = result.messages[0]
+			const secondMessage = result.messages[1]
+
+			expect(firstMessage.content).toHaveLength(2)
+			expect(firstMessage.content[1]).toHaveProperty("image")
+
+			expect(secondMessage.content).toHaveLength(2)
+			expect(secondMessage.content[1]).toHaveProperty("image")
+		})
+
+		it("should limit images when over AWS Bedrock limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+
+			// Create 25 messages with 1 image each (5 over the limit)
+			for (let i = 0; i < 25; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "text", text: `Browser screenshot ${i + 1}` },
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/png", data: VALID_BASE64_IMAGE },
+						},
+					],
+				})
+			}
+
+			// Access the private method for testing
+			const result = (handler as any).convertToBedrockConverseMessages(messages, "System prompt")
+
+			// Should have 25 messages
+			expect(result.messages).toHaveLength(25)
+
+			// Count actual images in the result
+			let imageCount = 0
+			let textPlaceholderCount = 0
+
+			for (const message of result.messages) {
+				for (const block of message.content) {
+					if (block.image) {
+						imageCount++
+					} else if (block.text && block.text.includes("[Image removed due to conversation limit")) {
+						textPlaceholderCount++
+					}
+				}
+			}
+
+			// Should have exactly 20 images and 5 text placeholders
+			expect(imageCount).toBe(AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION)
+			expect(textPlaceholderCount).toBe(5)
+		})
+
+		it("should preserve text content when limiting images", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+
+			// Create 22 messages with mixed content (2 over the limit)
+			for (let i = 0; i < 22; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "text", text: `Important context ${i + 1}` },
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/png", data: VALID_BASE64_IMAGE },
+						},
+						{ type: "text", text: `Additional info ${i + 1}` },
+					],
+				})
+			}
+
+			// Access the private method for testing
+			const result = (handler as any).convertToBedrockConverseMessages(messages, "System prompt")
+
+			// All text content should be preserved
+			for (let i = 0; i < 22; i++) {
+				const message = result.messages[i]
+				expect(message.content[0].text).toBe(`Important context ${i + 1}`)
+				expect(message.content[2].text).toBe(`Additional info ${i + 1}`)
+			}
+
+			// First 2 messages should have image placeholders
+			expect(result.messages[0].content[1].text).toBe(
+				"[Image removed due to conversation limit - Browser tool screenshot]",
+			)
+			expect(result.messages[1].content[1].text).toBe(
+				"[Image removed due to conversation limit - Browser tool screenshot]",
+			)
+
+			// Remaining messages should have images
+			for (let i = 2; i < 22; i++) {
+				expect(result.messages[i].content[1]).toHaveProperty("image")
+			}
+		})
+
+		it("should handle exactly 20 images without modification", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+
+			// Create exactly 20 messages with 1 image each
+			for (let i = 0; i < AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "text", text: `Message ${i + 1}` },
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/png", data: VALID_BASE64_IMAGE },
+						},
+					],
+				})
+			}
+
+			// Access the private method for testing
+			const result = (handler as any).convertToBedrockConverseMessages(messages, "System prompt")
+
+			// Should have 20 messages with all images intact
+			expect(result.messages).toHaveLength(20)
+
+			let imageCount = 0
+			for (const message of result.messages) {
+				for (const block of message.content) {
+					if (block.image) {
+						imageCount++
+					}
+				}
+			}
+
+			expect(imageCount).toBe(AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION)
+		})
+
+		it("should handle mixed message types correctly", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{ role: "user", content: "Text only message" },
+				{
+					role: "assistant",
+					content: [{ type: "text", text: "I understand." }],
+				},
+			]
+
+			// Add 21 image messages to exceed the limit
+			for (let i = 0; i < 21; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/png", data: VALID_BASE64_IMAGE },
+						},
+					],
+				})
+			}
+
+			// Access the private method for testing
+			const result = (handler as any).convertToBedrockConverseMessages(messages, "System prompt")
+
+			// Should have 23 messages total
+			expect(result.messages).toHaveLength(23)
+
+			// First two messages should be unchanged (no images)
+			expect(result.messages[0].content[0].text).toBe("Text only message")
+			expect(result.messages[1].content[0].text).toBe("I understand.")
+
+			// Count images in the result
+			let imageCount = 0
+			let placeholderCount = 0
+
+			for (const message of result.messages) {
+				for (const block of message.content) {
+					if (block.image) {
+						imageCount++
+					} else if (block.text && block.text.includes("[Image removed due to conversation limit")) {
+						placeholderCount++
+					}
+				}
+			}
+
+			// Should have exactly 20 images and 1 placeholder
+			expect(imageCount).toBe(20)
+			expect(placeholderCount).toBe(1)
+		})
+
+		it("should work with system message", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+
+			// Create 22 messages with images (2 over limit)
+			for (let i = 0; i < 22; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{
+							type: "image",
+							source: { type: "base64", media_type: "image/png", data: VALID_BASE64_IMAGE },
+						},
+					],
+				})
+			}
+
+			const systemMessage = "You are a helpful assistant that can analyze images."
+
+			// Access the private method for testing
+			const result = (handler as any).convertToBedrockConverseMessages(messages, systemMessage)
+
+			// System message should be preserved
+			expect(result.system).toHaveLength(1)
+			expect(result.system[0].text).toBe(systemMessage)
+
+			// Should have 22 messages with limited images
+			expect(result.messages).toHaveLength(22)
+
+			// Count images
+			let imageCount = 0
+			for (const message of result.messages) {
+				for (const block of message.content) {
+					if (block.image) {
+						imageCount++
+					}
+				}
+			}
+
+			expect(imageCount).toBe(AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION)
+		})
+	})
+})
diff --git a/src/api/providers/bedrock.ts b/src/api/providers/bedrock.ts
index 76e502e6c7..485b75c80b 100644
--- a/src/api/providers/bedrock.ts
+++ b/src/api/providers/bedrock.ts
@@ -30,6 +30,7 @@ import { MultiPointStrategy } from "../transform/cache-strategy/multi-point-stra
 import { ModelInfo as CacheModelInfo } from "../transform/cache-strategy/types"
 import { convertToBedrockConverseMessages as sharedConverter } from "../transform/bedrock-converse-format"
 import { getModelParams } from "../transform/model-params"
+import { limitImagesInConversation, hasExceededImageLimit } from "../transform/image-limiting"
 import { shouldUseReasoningBudget } from "../../shared/api"
 import type { SingleCompletionHandler, ApiHandlerCreateMessageMetadata } from "../index"
 
@@ -706,8 +707,20 @@ export class AwsBedrockHandler extends BaseProvider implements SingleCompletionH
 		modelInfo?: any,
 		conversationId?: string, // Optional conversation ID to track cache points across messages
 	): { system: SystemContentBlock[]; messages: Message[] } {
+		// Apply image limiting for AWS Bedrock's 20-image conversation limit
+		const limitedMessages = limitImagesInConversation(anthropicMessages as Anthropic.Messages.MessageParam[])
+
+		// Log if images were removed due to the limit
+		if (hasExceededImageLimit(anthropicMessages as Anthropic.Messages.MessageParam[])) {
+			logger.info("Applied image limiting for AWS Bedrock conversation", {
+				ctx: "bedrock",
+				originalImageCount: limitedMessages.length,
+				action: "removed_oldest_images_to_stay_within_limit",
+			})
+		}
+
 		// First convert messages using shared converter for proper image handling
-		const convertedMessages = sharedConverter(anthropicMessages as Anthropic.Messages.MessageParam[])
+		const convertedMessages = sharedConverter(limitedMessages)
 
 		// If prompt caching is disabled, return the converted messages directly
 		if (!usePromptCache) {
@@ -1121,6 +1134,21 @@ Suggestions:
 `,
 			logLevel: "error",
 		},
+		TOO_MANY_IMAGES: {
+			patterns: ["too many images", "too many images and documents", "images and documents:", "> 20"],
+			messageTemplate: `AWS Bedrock "too many images" error detected.
+
+This error occurs when the conversation contains more than 20 images total. The application has automatically applied image limiting to prevent this error in future requests.
+
+What happened:
+- AWS Bedrock has a hard limit of 20 images per conversation
+- Your conversation exceeded this limit (likely from Browser tool screenshots)
+- The oldest images have been automatically replaced with text placeholders
+- The conversation can now continue normally
+
+No action needed - the issue has been resolved automatically.`,
+			logLevel: "info",
+		},
 		SERVICE_QUOTA_EXCEEDED: {
 			patterns: ["service quota exceeded", "service quota", "quota exceeded for model"],
 			messageTemplate: `Service quota exceeded. This error indicates you've reached AWS service limits.
@@ -1234,6 +1262,7 @@ Please check:
 		const errorTypeOrder = [
 			"SERVICE_QUOTA_EXCEEDED", // Most specific - check before THROTTLING
 			"MODEL_NOT_READY",
+			"TOO_MANY_IMAGES", // Check before TOO_MANY_TOKENS for specificity
 			"TOO_MANY_TOKENS",
 			"INTERNAL_SERVER_ERROR",
 			"ON_DEMAND_NOT_SUPPORTED",
diff --git a/src/api/transform/__tests__/image-limiting.spec.ts b/src/api/transform/__tests__/image-limiting.spec.ts
new file mode 100644
index 0000000000..90c7d117bd
--- /dev/null
+++ b/src/api/transform/__tests__/image-limiting.spec.ts
@@ -0,0 +1,323 @@
+import { describe, it, expect } from "vitest"
+import { Anthropic } from "@anthropic-ai/sdk"
+import {
+	countImagesInConversation,
+	limitImagesInConversation,
+	hasExceededImageLimit,
+	AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION,
+} from "../image-limiting"
+
+describe("image-limiting", () => {
+	describe("countImagesInConversation", () => {
+		it("should count zero images in empty conversation", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+			expect(countImagesInConversation(messages)).toBe(0)
+		})
+
+		it("should count zero images in text-only conversation", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{ role: "user", content: "Hello" },
+				{ role: "assistant", content: "Hi there!" },
+			]
+			expect(countImagesInConversation(messages)).toBe(0)
+		})
+
+		it("should count images in single message", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "Look at this image:" },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data" } },
+						{ type: "image", source: { type: "base64", media_type: "image/jpeg", data: "base64data2" } },
+					],
+				},
+			]
+			expect(countImagesInConversation(messages)).toBe(2)
+		})
+
+		it("should count images across multiple messages", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "First image:" },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data1" } },
+					],
+				},
+				{ role: "assistant", content: "I see the image." },
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "Second and third images:" },
+						{ type: "image", source: { type: "base64", media_type: "image/jpeg", data: "base64data2" } },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data3" } },
+					],
+				},
+			]
+			expect(countImagesInConversation(messages)).toBe(3)
+		})
+
+		it("should handle mixed content types", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "Text content" },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data" } },
+						{ type: "text", text: "More text" },
+					],
+				},
+			]
+			expect(countImagesInConversation(messages)).toBe(1)
+		})
+	})
+
+	describe("hasExceededImageLimit", () => {
+		it("should return false when under limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data" } },
+					],
+				},
+			]
+			expect(hasExceededImageLimit(messages)).toBe(false)
+		})
+
+		it("should return false when exactly at limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+			// Create exactly 20 images
+			for (let i = 0; i < AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: `base64data${i}` } },
+					],
+				})
+			}
+			expect(hasExceededImageLimit(messages)).toBe(false)
+		})
+
+		it("should return true when over limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+			// Create 21 images (1 over limit)
+			for (let i = 0; i < AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION + 1; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: `base64data${i}` } },
+					],
+				})
+			}
+			expect(hasExceededImageLimit(messages)).toBe(true)
+		})
+
+		it("should work with custom limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data1" } },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data2" } },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data3" } },
+					],
+				},
+			]
+			expect(hasExceededImageLimit(messages, 2)).toBe(true)
+			expect(hasExceededImageLimit(messages, 3)).toBe(false)
+			expect(hasExceededImageLimit(messages, 4)).toBe(false)
+		})
+	})
+
+	describe("limitImagesInConversation", () => {
+		it("should return unchanged messages when under limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "Hello" },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data" } },
+					],
+				},
+			]
+			const result = limitImagesInConversation(messages)
+			expect(result).toEqual(messages)
+		})
+
+		it("should return unchanged messages when exactly at limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+			// Create exactly 20 images
+			for (let i = 0; i < AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: `base64data${i}` } },
+					],
+				})
+			}
+			const result = limitImagesInConversation(messages)
+			expect(result).toEqual(messages)
+			expect(countImagesInConversation(result)).toBe(AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION)
+		})
+
+		it("should limit images when over limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+			// Create 25 images (5 over limit)
+			for (let i = 0; i < 25; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "text", text: `Message ${i}` },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: `base64data${i}` } },
+					],
+				})
+			}
+
+			const result = limitImagesInConversation(messages)
+
+			// Should have exactly 20 images after limiting
+			expect(countImagesInConversation(result)).toBe(AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION)
+
+			// First 5 images should be replaced with text placeholders
+			for (let i = 0; i < 5; i++) {
+				const content = result[i].content as any[]
+				expect(content[1].type).toBe("text")
+				expect(content[1].text).toBe("[Image removed due to conversation limit - Browser tool screenshot]")
+			}
+
+			// Last 20 images should remain as images
+			for (let i = 5; i < 25; i++) {
+				const content = result[i].content as any[]
+				expect(content[1].type).toBe("image")
+				expect(content[1].source.data).toBe(`base64data${i}`)
+			}
+		})
+
+		it("should preserve text content when limiting images", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "First message" },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "image1" } },
+						{ type: "text", text: "More text" },
+					],
+				},
+				{
+					role: "user",
+					content: [
+						{ type: "text", text: "Second message" },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "image2" } },
+					],
+				},
+			]
+
+			const result = limitImagesInConversation(messages, 1) // Limit to 1 image
+
+			// Should have exactly 1 image
+			expect(countImagesInConversation(result)).toBe(1)
+
+			// First image should be replaced, text should remain
+			const firstContent = result[0].content as any[]
+			expect(firstContent[0].type).toBe("text")
+			expect(firstContent[0].text).toBe("First message")
+			expect(firstContent[1].type).toBe("text")
+			expect(firstContent[1].text).toBe("[Image removed due to conversation limit - Browser tool screenshot]")
+			expect(firstContent[2].type).toBe("text")
+			expect(firstContent[2].text).toBe("More text")
+
+			// Second image should remain
+			const secondContent = result[1].content as any[]
+			expect(secondContent[0].type).toBe("text")
+			expect(secondContent[0].text).toBe("Second message")
+			expect(secondContent[1].type).toBe("image")
+			expect(secondContent[1].source.data).toBe("image2")
+		})
+
+		it("should not mutate original messages", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "image1" } },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "image2" } },
+					],
+				},
+			]
+
+			const originalContent = JSON.parse(JSON.stringify(messages))
+			limitImagesInConversation(messages, 1)
+
+			// Original messages should be unchanged
+			expect(messages).toEqual(originalContent)
+		})
+
+		it("should work with custom limit", () => {
+			const messages: Anthropic.Messages.MessageParam[] = []
+			// Create 5 images
+			for (let i = 0; i < 5; i++) {
+				messages.push({
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: `base64data${i}` } },
+					],
+				})
+			}
+
+			const result = limitImagesInConversation(messages, 3) // Limit to 3 images
+
+			// Should have exactly 3 images
+			expect(countImagesInConversation(result)).toBe(3)
+
+			// First 2 should be replaced with text
+			for (let i = 0; i < 2; i++) {
+				const content = result[i].content as any[]
+				expect(content[0].type).toBe("text")
+				expect(content[0].text).toBe("[Image removed due to conversation limit - Browser tool screenshot]")
+			}
+
+			// Last 3 should remain as images
+			for (let i = 2; i < 5; i++) {
+				const content = result[i].content as any[]
+				expect(content[0].type).toBe("image")
+				expect(content[0].source.data).toBe(`base64data${i}`)
+			}
+		})
+
+		it("should handle messages with string content", () => {
+			const messages: Anthropic.Messages.MessageParam[] = [
+				{ role: "user", content: "Text only message" },
+				{
+					role: "user",
+					content: [
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "image1" } },
+						{ type: "image", source: { type: "base64", media_type: "image/png", data: "image2" } },
+					],
+				},
+			]
+
+			const result = limitImagesInConversation(messages, 1)
+
+			// Should have exactly 1 image
+			expect(countImagesInConversation(result)).toBe(1)
+
+			// String content should remain unchanged
+			expect(result[0].content).toBe("Text only message")
+
+			// First image should be replaced, second should remain
+			const arrayContent = result[1].content as any[]
+			expect(arrayContent[0].type).toBe("text")
+			expect(arrayContent[0].text).toBe("[Image removed due to conversation limit - Browser tool screenshot]")
+			expect(arrayContent[1].type).toBe("image")
+			expect(arrayContent[1].source.data).toBe("image2")
+		})
+	})
+
+	describe("AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION constant", () => {
+		it("should be set to 20", () => {
+			expect(AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION).toBe(20)
+		})
+	})
+})
diff --git a/src/api/transform/image-limiting.ts b/src/api/transform/image-limiting.ts
new file mode 100644
index 0000000000..d7585de11e
--- /dev/null
+++ b/src/api/transform/image-limiting.ts
@@ -0,0 +1,93 @@
+import { Anthropic } from "@anthropic-ai/sdk"
+
+/**
+ * AWS Bedrock has a hard limit of 20 images total per conversation.
+ * This constant defines that limit.
+ */
+export const AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION = 20
+
+/**
+ * Counts the total number of images across all messages in the conversation history
+ */
+export function countImagesInConversation(messages: Anthropic.Messages.MessageParam[]): number {
+	let totalImages = 0
+
+	for (const message of messages) {
+		if (Array.isArray(message.content)) {
+			for (const block of message.content) {
+				if (block.type === "image") {
+					totalImages++
+				}
+			}
+		}
+	}
+
+	return totalImages
+}
+
+/**
+ * Limits the total number of images in a conversation to the specified maximum.
+ * When the limit is exceeded, removes the oldest images while preserving the most recent ones.
+ * This ensures AWS Bedrock's 20-image limit is respected.
+ *
+ * @param messages - The conversation messages
+ * @param maxImages - Maximum number of images allowed (default: AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION)
+ * @returns Modified messages with image count limited to maxImages
+ */
+export function limitImagesInConversation(
+	messages: Anthropic.Messages.MessageParam[],
+	maxImages: number = AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION,
+): Anthropic.Messages.MessageParam[] {
+	const totalImages = countImagesInConversation(messages)
+
+	// If we're within the limit, return messages unchanged
+	if (totalImages <= maxImages) {
+		return messages
+	}
+
+	// We need to remove (totalImages - maxImages) images, starting from the oldest
+	const imagesToRemove = totalImages - maxImages
+	let imagesRemoved = 0
+
+	// Create a deep copy of messages to avoid mutating the original
+	const modifiedMessages = messages.map((message) => ({
+		...message,
+		content: Array.isArray(message.content) ? message.content.map((block) => ({ ...block })) : message.content,
+	}))
+
+	// Iterate through messages from oldest to newest, removing images until we reach the limit
+	for (let i = 0; i < modifiedMessages.length && imagesRemoved < imagesToRemove; i++) {
+		const message = modifiedMessages[i]
+
+		if (Array.isArray(message.content)) {
+			const newContent = []
+
+			for (const block of message.content) {
+				if (block.type === "image" && imagesRemoved < imagesToRemove) {
+					// Replace image with a text placeholder
+					newContent.push({
+						type: "text" as const,
+						text: "[Image removed due to conversation limit - Browser tool screenshot]",
+					})
+					imagesRemoved++
+				} else {
+					newContent.push(block)
+				}
+			}
+
+			message.content = newContent
+		}
+	}
+
+	return modifiedMessages
+}
+
+/**
+ * Checks if a conversation has exceeded the AWS Bedrock image limit
+ */
+export function hasExceededImageLimit(
+	messages: Anthropic.Messages.MessageParam[],
+	maxImages: number = AWS_BEDROCK_MAX_IMAGES_PER_CONVERSATION,
+): boolean {
+	return countImagesInConversation(messages) > maxImages
+}