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diff --git a/llama.cpp/tools/server/webui/tests/unit/clipboard.test.ts b/llama.cpp/tools/server/webui/tests/unit/clipboard.test.ts
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--- /dev/null
+++ b/llama.cpp/tools/server/webui/tests/unit/clipboard.test.ts
@@ -0,0 +1,423 @@
+import { describe, it, expect } from 'vitest';
+import { AttachmentType } from '$lib/enums';
+import {
+	formatMessageForClipboard,
+	parseClipboardContent,
+	hasClipboardAttachments
+} from '$lib/utils/clipboard';
+
+describe('formatMessageForClipboard', () => {
+	it('returns plain content when no extras', () => {
+		const result = formatMessageForClipboard('Hello world', undefined);
+		expect(result).toBe('Hello world');
+	});
+
+	it('returns plain content when extras is empty array', () => {
+		const result = formatMessageForClipboard('Hello world', []);
+		expect(result).toBe('Hello world');
+	});
+
+	it('handles empty string content', () => {
+		const result = formatMessageForClipboard('', undefined);
+		expect(result).toBe('');
+	});
+
+	it('returns plain content when extras has only non-text attachments', () => {
+		const extras = [
+			{
+				type: AttachmentType.IMAGE as const,
+				name: 'image.png',
+				base64Url: 'data:image/png;base64,...'
+			}
+		];
+		const result = formatMessageForClipboard('Hello world', extras);
+		expect(result).toBe('Hello world');
+	});
+
+	it('filters non-text attachments and keeps only text ones', () => {
+		const extras = [
+			{
+				type: AttachmentType.IMAGE as const,
+				name: 'image.png',
+				base64Url: 'data:image/png;base64,...'
+			},
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file.txt',
+				content: 'Text content'
+			},
+			{
+				type: AttachmentType.PDF as const,
+				name: 'doc.pdf',
+				base64Data: 'data:application/pdf;base64,...',
+				content: 'PDF content',
+				processedAsImages: false
+			}
+		];
+		const result = formatMessageForClipboard('Hello', extras);
+
+		expect(result).toContain('"file.txt"');
+		expect(result).not.toContain('image.png');
+		expect(result).not.toContain('doc.pdf');
+	});
+
+	it('formats message with text attachments', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file1.txt',
+				content: 'File 1 content'
+			},
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file2.txt',
+				content: 'File 2 content'
+			}
+		];
+		const result = formatMessageForClipboard('Hello world', extras);
+
+		expect(result).toContain('"Hello world"');
+		expect(result).toContain('"type": "TEXT"');
+		expect(result).toContain('"name": "file1.txt"');
+		expect(result).toContain('"content": "File 1 content"');
+		expect(result).toContain('"name": "file2.txt"');
+	});
+
+	it('handles content with quotes and special characters', () => {
+		const content = 'Hello "world" with\nnewline';
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'test.txt',
+				content: 'Test content'
+			}
+		];
+		const result = formatMessageForClipboard(content, extras);
+
+		// Should be valid JSON
+		expect(result.startsWith('"')).toBe(true);
+		// The content should be properly escaped
+		const parsed = JSON.parse(result.split('\n')[0]);
+		expect(parsed).toBe(content);
+	});
+
+	it('converts legacy context type to TEXT type', () => {
+		const extras = [
+			{
+				type: AttachmentType.LEGACY_CONTEXT as const,
+				name: 'legacy.txt',
+				content: 'Legacy content'
+			}
+		];
+		const result = formatMessageForClipboard('Hello', extras);
+
+		expect(result).toContain('"type": "TEXT"');
+		expect(result).not.toContain('"context"');
+	});
+
+	it('handles attachment content with special characters', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'code.js',
+				content: 'const x = "hello\\nworld";\nconst y = `template ${var}`;'
+			}
+		];
+		const formatted = formatMessageForClipboard('Check this code', extras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.textAttachments[0].content).toBe(
+			'const x = "hello\\nworld";\nconst y = `template ${var}`;'
+		);
+	});
+
+	it('handles unicode characters in content and attachments', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'unicode.txt',
+				content: '日本語テスト 🎉 émojis'
+			}
+		];
+		const formatted = formatMessageForClipboard('Привет мир 👋', extras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.message).toBe('Привет мир 👋');
+		expect(parsed.textAttachments[0].content).toBe('日本語テスト 🎉 émojis');
+	});
+
+	it('formats as plain text when asPlainText is true', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file1.txt',
+				content: 'File 1 content'
+			},
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file2.txt',
+				content: 'File 2 content'
+			}
+		];
+		const result = formatMessageForClipboard('Hello world', extras, true);
+
+		expect(result).toBe('Hello world\n\nFile 1 content\n\nFile 2 content');
+	});
+
+	it('returns plain content when asPlainText is true but no attachments', () => {
+		const result = formatMessageForClipboard('Hello world', [], true);
+		expect(result).toBe('Hello world');
+	});
+
+	it('plain text mode does not use JSON format', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'test.txt',
+				content: 'Test content'
+			}
+		];
+		const result = formatMessageForClipboard('Hello', extras, true);
+
+		expect(result).not.toContain('"type"');
+		expect(result).not.toContain('[');
+		expect(result).toBe('Hello\n\nTest content');
+	});
+});
+
+describe('parseClipboardContent', () => {
+	it('returns plain text as message when not in special format', () => {
+		const result = parseClipboardContent('Hello world');
+
+		expect(result.message).toBe('Hello world');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('handles empty string input', () => {
+		const result = parseClipboardContent('');
+
+		expect(result.message).toBe('');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('handles whitespace-only input', () => {
+		const result = parseClipboardContent('   \n\t  ');
+
+		expect(result.message).toBe('   \n\t  ');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('returns plain text as message when starts with quote but invalid format', () => {
+		const result = parseClipboardContent('"Unclosed quote');
+
+		expect(result.message).toBe('"Unclosed quote');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('returns original text when JSON array is malformed', () => {
+		const input = '"Hello"\n[invalid json';
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('"Hello"\n[invalid json');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('parses message with text attachments', () => {
+		const input = `"Hello world"
+[
+  {"type":"TEXT","name":"file1.txt","content":"File 1 content"},
+  {"type":"TEXT","name":"file2.txt","content":"File 2 content"}
+]`;
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('Hello world');
+		expect(result.textAttachments).toHaveLength(2);
+		expect(result.textAttachments[0].name).toBe('file1.txt');
+		expect(result.textAttachments[0].content).toBe('File 1 content');
+		expect(result.textAttachments[1].name).toBe('file2.txt');
+		expect(result.textAttachments[1].content).toBe('File 2 content');
+	});
+
+	it('handles escaped quotes in message', () => {
+		const input = `"Hello \\"world\\" with quotes"
+[
+  {"type":"TEXT","name":"file.txt","content":"test"}
+]`;
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('Hello "world" with quotes');
+		expect(result.textAttachments).toHaveLength(1);
+	});
+
+	it('handles newlines in message', () => {
+		const input = `"Hello\\nworld"
+[
+  {"type":"TEXT","name":"file.txt","content":"test"}
+]`;
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('Hello\nworld');
+		expect(result.textAttachments).toHaveLength(1);
+	});
+
+	it('returns message only when no array follows', () => {
+		const input = '"Just a quoted string"';
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('Just a quoted string');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('filters out invalid attachment objects', () => {
+		const input = `"Hello"
+[
+  {"type":"TEXT","name":"valid.txt","content":"valid"},
+  {"type":"INVALID","name":"invalid.txt","content":"invalid"},
+  {"name":"missing-type.txt","content":"missing"},
+  {"type":"TEXT","content":"missing name"}
+]`;
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('Hello');
+		expect(result.textAttachments).toHaveLength(1);
+		expect(result.textAttachments[0].name).toBe('valid.txt');
+	});
+
+	it('handles empty attachments array', () => {
+		const input = '"Hello"\n[]';
+
+		const result = parseClipboardContent(input);
+
+		expect(result.message).toBe('Hello');
+		expect(result.textAttachments).toHaveLength(0);
+	});
+
+	it('roundtrips correctly with formatMessageForClipboard', () => {
+		const originalContent = 'Hello "world" with\nspecial characters';
+		const originalExtras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file1.txt',
+				content: 'Content with\nnewlines and "quotes"'
+			},
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file2.txt',
+				content: 'Another file'
+			}
+		];
+
+		const formatted = formatMessageForClipboard(originalContent, originalExtras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.message).toBe(originalContent);
+		expect(parsed.textAttachments).toHaveLength(2);
+		expect(parsed.textAttachments[0].name).toBe('file1.txt');
+		expect(parsed.textAttachments[0].content).toBe('Content with\nnewlines and "quotes"');
+		expect(parsed.textAttachments[1].name).toBe('file2.txt');
+		expect(parsed.textAttachments[1].content).toBe('Another file');
+	});
+});
+
+describe('hasClipboardAttachments', () => {
+	it('returns false for plain text', () => {
+		expect(hasClipboardAttachments('Hello world')).toBe(false);
+	});
+
+	it('returns false for empty string', () => {
+		expect(hasClipboardAttachments('')).toBe(false);
+	});
+
+	it('returns false for quoted string without attachments', () => {
+		expect(hasClipboardAttachments('"Hello world"')).toBe(false);
+	});
+
+	it('returns true for valid format with attachments', () => {
+		const input = `"Hello"
+[{"type":"TEXT","name":"file.txt","content":"test"}]`;
+
+		expect(hasClipboardAttachments(input)).toBe(true);
+	});
+
+	it('returns false for format with empty attachments array', () => {
+		const input = '"Hello"\n[]';
+
+		expect(hasClipboardAttachments(input)).toBe(false);
+	});
+
+	it('returns false for malformed JSON', () => {
+		expect(hasClipboardAttachments('"Hello"\n[broken')).toBe(false);
+	});
+});
+
+describe('roundtrip edge cases', () => {
+	it('preserves empty message with attachments', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'file.txt',
+				content: 'Content only'
+			}
+		];
+		const formatted = formatMessageForClipboard('', extras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.message).toBe('');
+		expect(parsed.textAttachments).toHaveLength(1);
+		expect(parsed.textAttachments[0].content).toBe('Content only');
+	});
+
+	it('preserves attachment with empty content', () => {
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'empty.txt',
+				content: ''
+			}
+		];
+		const formatted = formatMessageForClipboard('Message', extras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.message).toBe('Message');
+		expect(parsed.textAttachments).toHaveLength(1);
+		expect(parsed.textAttachments[0].content).toBe('');
+	});
+
+	it('preserves multiple backslashes', () => {
+		const content = 'Path: C:\\\\Users\\\\test\\\\file.txt';
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'path.txt',
+				content: 'D:\\\\Data\\\\file'
+			}
+		];
+		const formatted = formatMessageForClipboard(content, extras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.message).toBe(content);
+		expect(parsed.textAttachments[0].content).toBe('D:\\\\Data\\\\file');
+	});
+
+	it('preserves tabs and various whitespace', () => {
+		const content = 'Line1\t\tTabbed\n  Spaced\r\nCRLF';
+		const extras = [
+			{
+				type: AttachmentType.TEXT as const,
+				name: 'whitespace.txt',
+				content: '\t\t\n\n   '
+			}
+		];
+		const formatted = formatMessageForClipboard(content, extras);
+		const parsed = parseClipboardContent(formatted);
+
+		expect(parsed.message).toBe(content);
+		expect(parsed.textAttachments[0].content).toBe('\t\t\n\n   ');
+	});
+});