diff --git a/packages/tui/CHANGELOG.md b/packages/tui/CHANGELOG.md
index cf985f22..ee72172e 100644
--- a/packages/tui/CHANGELOG.md
+++ b/packages/tui/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Fixed `isImageLine()` to check for image escape sequences anywhere in a line, not just at the start. This prevents TUI crashes when rendering lines containing image data. ([#1091](https://github.com/badlogic/pi-mono/pull/1091) by [@zedrdave](https://github.com/zedrdave))
+
 ## [0.50.4] - 2026-01-30
 
 ### Added
diff --git a/packages/tui/src/terminal-image.ts b/packages/tui/src/terminal-image.ts
index 0a504a46..0199ac94 100644
--- a/packages/tui/src/terminal-image.ts
+++ b/packages/tui/src/terminal-image.ts
@@ -79,24 +79,12 @@ export function getCapabilities(): TerminalCapabilities {
 
 export function resetCapabilitiesCache(): void {
 	cachedCapabilities = null;
-	imageEscapePrefix = undefined;
-}
-
-let imageEscapePrefix: string | null | undefined;
-
-function getImageEscapePrefix(): string | null {
-	if (imageEscapePrefix === undefined) {
-		const protocol = getCapabilities().images;
-		if (protocol === "kitty") imageEscapePrefix = "\x1b_G";
-		else if (protocol === "iterm2") imageEscapePrefix = "\x1b]1337;File=";
-		else imageEscapePrefix = null;
-	}
-	return imageEscapePrefix;
 }
 
 export function isImageLine(line: string): boolean {
-	const prefix = getImageEscapePrefix();
-	return prefix !== null && line.startsWith(prefix);
+	// Check for Kitty or iTerm2 image escape sequences anywhere in the line
+	// This prevents width checks from failing on lines containing image data
+	return line.includes("\x1b_G") || line.includes("\x1b]1337;File=");
 }
 
 /**
diff --git a/packages/tui/test/bug-regression-isimageline-startswith-bug.test.ts b/packages/tui/test/bug-regression-isimageline-startswith-bug.test.ts
new file mode 100644
index 00000000..e5a5e417
--- /dev/null
+++ b/packages/tui/test/bug-regression-isimageline-startswith-bug.test.ts
@@ -0,0 +1,280 @@
+/**
+ * Bug regression test for isImageLine() crash scenario
+ *
+ * Bug: When isImageLine() used startsWith() and terminal doesn't support images,
+ * it would return false for lines containing image escape sequences, causing TUI to
+ * crash with "Rendered line exceeds terminal width" error.
+ *
+ * Fix: Changed to use includes() to detect escape sequences anywhere in the line.
+ *
+ * This test demonstrates:
+ * 1. The bug scenario with the old implementation
+ * 2. That the fix works correctly
+ */
+
+import assert from "node:assert";
+import { describe, it } from "node:test";
+
+describe("Bug regression: isImageLine() crash with image escape sequences", () => {
+	describe("Bug scenario: Terminal without image support", () => {
+		it("old implementation would return false, causing crash", () => {
+			/**
+			 * OLD IMPLEMENTATION (buggy):
+			 * ```typescript
+			 * export function isImageLine(line: string): boolean {
+			 *   const prefix = getImageEscapePrefix();
+			 *   return prefix !== null && line.startsWith(prefix);
+			 * }
+			 * ```
+			 *
+			 * When terminal doesn't support images:
+			 * - getImageEscapePrefix() returns null
+			 * - isImageLine() returns false even for lines containing image sequences
+			 * - TUI performs width check on line containing 300KB+ of base64 data
+			 * - Crash: "Rendered line exceeds terminal width (304401 > 115)"
+			 */
+
+			// Simulate old implementation behavior
+			const oldIsImageLine = (line: string, imageEscapePrefix: string | null): boolean => {
+				return imageEscapePrefix !== null && line.startsWith(imageEscapePrefix);
+			};
+
+			// When terminal doesn't support images, prefix is null
+			const terminalWithoutImageSupport = null;
+
+			// Line containing image escape sequence with text before it (common bug scenario)
+			const lineWithImageSequence =
+				"Read image file [image/jpeg]\x1b]1337;File=size=800,600;inline=1:base64data...\x07";
+
+			// Old implementation would return false (BUG!)
+			const oldResult = oldIsImageLine(lineWithImageSequence, terminalWithoutImageSupport);
+			assert.strictEqual(
+				oldResult,
+				false,
+				"Bug: old implementation returns false for line containing image sequence when terminal has no image support",
+			);
+		});
+
+		it("new implementation returns true correctly", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			// Line containing image escape sequence with text before it
+			const lineWithImageSequence =
+				"Read image file [image/jpeg]\x1b]1337;File=size=800,600;inline=1:base64data...\x07";
+
+			// New implementation should return true (FIX!)
+			const newResult = isImageLine(lineWithImageSequence);
+			assert.strictEqual(
+				newResult,
+				true,
+				"Fix: new implementation returns true for line containing image sequence",
+			);
+		});
+
+		it("new implementation detects Kitty sequences in any position", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			const scenarios = [
+				"At start: \x1b_Ga=T,f=100,data...\x1b\\",
+				"Prefix \x1b_Ga=T,data...\x1b\\",
+				"Suffix text \x1b_Ga=T,data...\x1b\\ suffix",
+				"Middle \x1b_Ga=T,data...\x1b\\ more text",
+				// Very long line (simulating 300KB+ crash scenario)
+				"Text before " +
+					"\x1b_Ga=T,f=100" +
+					"A".repeat(300000) +
+					" text after",
+			];
+
+			for (const line of scenarios) {
+				assert.strictEqual(
+					isImageLine(line),
+					true,
+					`Should detect Kitty sequence in: ${line.slice(0, 50)}...`,
+				);
+			}
+		});
+
+		it("new implementation detects iTerm2 sequences in any position", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			const scenarios = [
+				"At start: \x1b]1337;File=size=100,100:base64...\x07",
+				"Prefix \x1b]1337;File=inline=1:data==\x07",
+				"Suffix text \x1b]1337;File=inline=1:data==\x07 suffix",
+				"Middle \x1b]1337;File=inline=1:data==\x07 more text",
+				// Very long line (simulating 304KB crash scenario)
+				"Text before " +
+					"\x1b]1337;File=size=800,600;inline=1:" +
+					"B".repeat(300000) +
+					" text after",
+			];
+
+			for (const line of scenarios) {
+				assert.strictEqual(
+					isImageLine(line),
+					true,
+					`Should detect iTerm2 sequence in: ${line.slice(0, 50)}...`,
+				);
+			}
+		});
+	});
+
+	describe("Integration: Tool execution scenario", () => {
+		/**
+		 * This simulates what happens when the `read` tool reads an image file.
+		 * The tool result contains both text and image content:
+		 *
+		 * ```typescript
+		 * {
+		 *   content: [
+		 *     { type: "text", text: "Read image file [image/jpeg]\n800x600" },
+		 *     { type: "image", data: "base64...", mimeType: "image/jpeg" }
+		 *   ]
+		 * }
+		 * ```
+		 *
+		 * When this is rendered, the image component creates escape sequences.
+		 * If isImageLine() doesn't detect them, TUI crashes.
+		 */
+
+		it("detects image sequences in read tool output", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			// Simulate output when read tool processes an image
+			// The line might have text from the read result plus the image escape sequence
+			const toolOutputLine =
+				"Read image file [image/jpeg]\x1b]1337;File=size=800,600;inline=1:base64image...\x07";
+
+			assert.strictEqual(
+				isImageLine(toolOutputLine),
+				true,
+				"Should detect image sequence in tool output line",
+			);
+		});
+
+		it("detects Kitty sequences from Image component", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			// Kitty image component creates multi-line output with escape sequences
+			const kittyLine = "\x1b_Ga=T,f=100,t=f,d=base64data...\x1b\\\x1b_Gm=i=1;\x1b\\";
+
+			assert.strictEqual(
+				isImageLine(kittyLine),
+				true,
+				"Should detect Kitty image component output",
+			);
+		});
+
+		it("handles ANSI codes before image sequences", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			// Line might have styling (error, warning, etc.) before image data
+			const lines = [
+				"\x1b[31mError\x1b[0m: \x1b]1337;File=inline=1:base64==\x07",
+				"\x1b[33mWarning\x1b[0m: \x1b_Ga=T,data...\x1b\\",
+				"\x1b[1mBold\x1b[0m \x1b]1337;File=:base64==\x07\x1b[0m",
+			];
+
+			for (const line of lines) {
+				assert.strictEqual(
+					isImageLine(line),
+					true,
+					`Should detect image sequence after ANSI codes: ${line.slice(0, 30)}...`,
+				);
+			}
+		});
+	});
+
+	describe("Crash scenario simulation", () => {
+		it("does NOT crash on very long lines with image sequences", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			/**
+			 * Simulate the exact crash scenario:
+			 * - Line is 304,401 characters (the crash log showed 58649 > 115)
+			 * - Contains image escape sequence somewhere in the middle
+			 * - Old implementation would return false, causing TUI to do width check
+			 * - New implementation returns true, skipping width check (preventing crash)
+			 */
+
+			const base64Char = "A".repeat(100);
+			const iterm2Sequence = "\x1b]1337;File=size=800,600;inline=1:";
+
+			// Build a line that would cause the crash
+			const crashLine =
+				"Output: " +
+				iterm2Sequence +
+				base64Char.repeat(3040) + // ~304,000 chars
+				" end of output";
+
+			// Verify line is very long
+			assert(crashLine.length > 300000, "Test line should be > 300KB");
+
+			// New implementation should detect it (prevents crash)
+			const detected = isImageLine(crashLine);
+			assert.strictEqual(
+				detected,
+				true,
+				"Should detect image sequence in very long line, preventing TUI crash",
+			);
+		});
+
+		it("handles lines exactly matching crash log dimensions", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			/**
+			 * Crash log showed: line 58649 chars wide, terminal width 115
+			 * Let's create a line with similar characteristics
+			 */
+
+			const targetWidth = 58649;
+			const prefix = "Text";
+			const sequence = "\x1b_Ga=T,f=100";
+			const suffix = "End";
+			const padding = "A".repeat(targetWidth - prefix.length - sequence.length - suffix.length);
+			const line = `${prefix}${sequence}${padding}${suffix}`;
+
+			assert.strictEqual(line.length, 58649);
+			assert.strictEqual(
+				isImageLine(line),
+				true,
+				"Should detect image sequence in 58649-char line",
+			);
+		});
+	});
+
+	describe("Negative cases: Don't false positive", () => {
+		it("does not detect images in regular long text", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			// Very long line WITHOUT image sequences
+			const longText = "A".repeat(100000);
+
+			assert.strictEqual(
+				isImageLine(longText),
+				false,
+				"Should not detect images in plain long text",
+			);
+		});
+
+		it("does not detect images in lines with file paths", async () => {
+			const { isImageLine } = await import("../src/terminal-image.js");
+
+			const filePaths = [
+				"/path/to/1337/image.jpg",
+				"/usr/local/bin/File_converter",
+				"~/Documents/1337File_backup.png",
+				"./_G_test_file.txt",
+			];
+
+			for (const path of filePaths) {
+				assert.strictEqual(
+					isImageLine(path),
+					false,
+					`Should not falsely detect image sequence in path: ${path}`,
+				);
+			}
+		});
+	});
+});
diff --git a/packages/tui/test/terminal-image.test.ts b/packages/tui/test/terminal-image.test.ts
new file mode 100644
index 00000000..b573837c
--- /dev/null
+++ b/packages/tui/test/terminal-image.test.ts
@@ -0,0 +1,153 @@
+/**
+ * Tests for terminal image detection and line handling
+ */
+
+import assert from "node:assert";
+import { describe, it } from "node:test";
+import { isImageLine } from "../src/terminal-image.js";
+
+describe("isImageLine", () => {
+	describe("iTerm2 image protocol", () => {
+		it("should detect iTerm2 image escape sequence at start of line", () => {
+			// iTerm2 image escape sequence: ESC ]1337;File=...
+			const iterm2ImageLine = "\x1b]1337;File=size=100,100;inline=1:base64encodeddata==\x07";
+			assert.strictEqual(isImageLine(iterm2ImageLine), true);
+		});
+
+		it("should detect iTerm2 image escape sequence with text before it", () => {
+			// Simulating a line that has text then image data (bug scenario)
+			const lineWithTextAndImage = "Some text \x1b]1337;File=size=100,100;inline=1:base64data==\x07 more text";
+			assert.strictEqual(isImageLine(lineWithTextAndImage), true);
+		});
+
+		it("should detect iTerm2 image escape sequence in middle of long line", () => {
+			// Simulate a very long line with image data in the middle
+			const longLineWithImage =
+				"Text before image..." + "\x1b]1337;File=inline=1:verylongbase64data==" + "...text after";
+			assert.strictEqual(isImageLine(longLineWithImage), true);
+		});
+
+		it("should detect iTerm2 image escape sequence at end of line", () => {
+			const lineWithImageAtEnd = "Regular text ending with \x1b]1337;File=inline=1:base64data==\x07";
+			assert.strictEqual(isImageLine(lineWithImageAtEnd), true);
+		});
+
+		it("should detect minimal iTerm2 image escape sequence", () => {
+			const minimalImageLine = "\x1b]1337;File=:\x07";
+			assert.strictEqual(isImageLine(minimalImageLine), true);
+		});
+	});
+
+	describe("Kitty image protocol", () => {
+		it("should detect Kitty image escape sequence at start of line", () => {
+			// Kitty image escape sequence: ESC _G
+			const kittyImageLine = "\x1b_Ga=T,f=100,t=f,d=base64data...\x1b\\\x1b_Gm=i=1;\x1b\\";
+			assert.strictEqual(isImageLine(kittyImageLine), true);
+		});
+
+		it("should detect Kitty image escape sequence with text before it", () => {
+			// Bug scenario: text + image data in same line
+			const lineWithTextAndKittyImage = "Output: \x1b_Ga=T,f=100;data...\x1b\\\x1b_Gm=i=1;\x1b\\";
+			assert.strictEqual(isImageLine(lineWithTextAndKittyImage), true);
+		});
+
+		it("should detect Kitty image escape sequence with padding", () => {
+			// Kitty protocol adds padding to escape sequences
+			const kittyWithPadding = "  \x1b_Ga=T,f=100...\x1b\\\x1b_Gm=i=1;\x1b\\  ";
+			assert.strictEqual(isImageLine(kittyWithPadding), true);
+		});
+	});
+
+	describe("Bug regression tests", () => {
+		it("should detect image sequences in very long lines (304k+ chars)", () => {
+			// This simulates the crash scenario: a line with 304,401 chars
+			// containing image escape sequences somewhere
+			const base64Char = "A".repeat(100); // 100 chars of base64-like data
+			const imageSequence = "\x1b]1337;File=size=800,600;inline=1:";
+
+			// Build a long line with image sequence
+			const longLine =
+				"Text prefix " +
+				imageSequence +
+				base64Char.repeat(3000) + // ~300,000 chars
+				" suffix";
+
+			assert.strictEqual(longLine.length > 300000, true);
+			assert.strictEqual(isImageLine(longLine), true);
+		});
+
+		it("should detect image sequences when terminal doesn't support images", () => {
+			// The bug occurred when getImageEscapePrefix() returned null
+			// isImageLine should still detect image sequences regardless
+			const lineWithImage = "Read image file [image/jpeg]\x1b]1337;File=inline=1:base64data==\x07";
+			assert.strictEqual(isImageLine(lineWithImage), true);
+		});
+
+		it("should detect image sequences with ANSI codes before them", () => {
+			// Text might have ANSI styling before image data
+			const lineWithAnsiAndImage = "\x1b[31mError output \x1b]1337;File=inline=1:image==\x07";
+			assert.strictEqual(isImageLine(lineWithAnsiAndImage), true);
+		});
+
+		it("should detect image sequences with ANSI codes after them", () => {
+			const lineWithImageAndAnsi = "\x1b_Ga=T,f=100:data...\x1b\\\x1b_Gm=i=1;\x1b\\\x1b[0m reset";
+			assert.strictEqual(isImageLine(lineWithImageAndAnsi), true);
+		});
+	});
+
+	describe("Negative cases - lines without images", () => {
+		it("should not detect images in plain text lines", () => {
+			const plainText = "This is just a regular text line without any escape sequences";
+			assert.strictEqual(isImageLine(plainText), false);
+		});
+
+		it("should not detect images in lines with only ANSI codes", () => {
+			const ansiText = "\x1b[31mRed text\x1b[0m and \x1b[32mgreen text\x1b[0m";
+			assert.strictEqual(isImageLine(ansiText), false);
+		});
+
+		it("should not detect images in lines with cursor movement codes", () => {
+			const cursorCodes = "\x1b[1A\x1b[2KLine cleared and moved up";
+			assert.strictEqual(isImageLine(cursorCodes), false);
+		});
+
+		it("should not detect images in lines with partial iTerm2 sequences", () => {
+			// Similar prefix but missing the complete sequence
+			const partialSequence = "Some text with ]1337;File but missing ESC at start";
+			assert.strictEqual(isImageLine(partialSequence), false);
+		});
+
+		it("should not detect images in lines with partial Kitty sequences", () => {
+			// Similar prefix but missing the complete sequence
+			const partialSequence = "Some text with _G but missing ESC at start";
+			assert.strictEqual(isImageLine(partialSequence), false);
+		});
+
+		it("should not detect images in empty lines", () => {
+			assert.strictEqual(isImageLine(""), false);
+		});
+
+		it("should not detect images in lines with newlines only", () => {
+			assert.strictEqual(isImageLine("\n"), false);
+			assert.strictEqual(isImageLine("\n\n"), false);
+		});
+	});
+
+	describe("Mixed content scenarios", () => {
+		it("should detect images when line has both Kitty and iTerm2 sequences", () => {
+			const mixedLine = "Kitty: \x1b_Ga=T...\x1b\\\x1b_Gm=i=1;\x1b\\ iTerm2: \x1b]1337;File=inline=1:data==\x07";
+			assert.strictEqual(isImageLine(mixedLine), true);
+		});
+
+		it("should detect image in line with multiple text and image segments", () => {
+			const complexLine = "Start \x1b]1337;File=img1==\x07 middle \x1b]1337;File=img2==\x07 end";
+			assert.strictEqual(isImageLine(complexLine), true);
+		});
+
+		it("should not falsely detect image in line with file path containing keywords", () => {
+			// File path might contain "1337" or "File" but without escape sequences
+			const filePathLine = "/path/to/File_1337_backup/image.jpg";
+			assert.strictEqual(isImageLine(filePathLine), false);
+		});
+	});
+});