diff --git a/src/services/tokenEstimation.ts b/src/services/tokenEstimation.ts
index acaef7a5..53471dc6 100644
--- a/src/services/tokenEstimation.ts
+++ b/src/services/tokenEstimation.ts
@@ -223,6 +223,49 @@ export function bytesPerTokenForFileType(fileExtension: string): number {
   }
 }
 
+/**
+ * Tokenizer ratio by model family.
+ * Different models have different encodings.
+ */
+export interface ModelTokenizerConfig {
+  modelFamily: string
+  bytesPerToken: number
+  supportsJson: boolean
+  supportsCode: boolean
+}
+
+export const MODEL_TOKENIZER_CONFIGS: ModelTokenizerConfig[] = [
+  { modelFamily: 'claude', bytesPerToken: 3.5, supportsJson: true, supportsCode: true },
+  { modelFamily: 'gpt-4', bytesPerToken: 4, supportsJson: true, supportsCode: true },
+  { modelFamily: 'gpt-3.5', bytesPerToken: 4, supportsJson: true, supportsCode: true },
+  { modelFamily: 'gemini', bytesPerToken: 3.5, supportsJson: true, supportsCode: true },
+  { modelFamily: 'llama', bytesPerToken: 3.8, supportsJson: true, supportsCode: true },
+  { modelFamily: 'deepseek', bytesPerToken: 3.5, supportsJson: true, supportsCode: true },
+  { modelFamily: 'minimax', bytesPerToken: 3.2, supportsJson: true, supportsCode: true },
+]
+
+/**
+ * Get tokenizer config for a model.
+ */
+export function getTokenizerConfig(model: string): ModelTokenizerConfig {
+  const lower = model.toLowerCase()
+  
+  for (const config of MODEL_TOKENIZER_CONFIGS) {
+    if (lower.includes(config.modelFamily)) {
+      return config
+    }
+  }
+  
+  return { modelFamily: 'unknown', bytesPerToken: 4, supportsJson: true, supportsCode: true }
+}
+
+/**
+ * Get bytes-per-token ratio for a model.
+ */
+export function getBytesPerTokenForModel(model: string): number {
+  return getTokenizerConfig(model).bytesPerToken
+}
+
 /**
  * Like {@link roughTokenCountEstimation} but uses a more accurate
  * bytes-per-token ratio when the file type is known.
@@ -241,6 +284,106 @@ export function roughTokenCountEstimationForFileType(
   )
 }
 
+/**
+ * Content type classification for compression ratio.
+ */
+export type ContentType = 
+  | 'json' | 'code' | 'prose' | 'technical' 
+  | 'list' | 'table' | 'mixed'
+
+/**
+ * Compression ratio by content type.
+ * Measured empirically - denser content = lower ratio.
+ */
+export const COMPRESSION_RATIOS: Record<ContentType, { min: number; max: number; typical: number }> = {
+  json: { min: 1.5, max: 2.5, typical: 2 },
+  code: { min: 3, max: 4.5, typical: 3.5 },
+  prose: { min: 3.5, max: 4.5, typical: 4 },
+  technical: { min: 2.5, max: 3.5, typical: 3 },
+  list: { min: 2, max: 3, typical: 2.5 },
+  table: { min: 1.8, max: 2.8, typical: 2.2 },
+  mixed: { min: 3, max: 4, typical: 3.5 },
+}
+
+/**
+ * Detect content type from content.
+ */
+export function detectContentType(content: string): ContentType {
+  const trimmed = content.trim()
+  
+  // JSON
+  if ((trimmed.startsWith('{') && trimmed.endsWith('}')) || 
+      (trimmed.startsWith('[') && trimmed.endsWith(']'))) {
+    try {
+      JSON.parse(trimmed)
+      return 'json'
+    } catch { /* not valid json */ }
+  }
+  
+  // Table (tabs or consistent delimiters)
+  const lines = trimmed.split('\n')
+  if (lines.length > 2) {
+    const hasTabs = lines[0].includes('\t')
+    const hasCommas = lines[0].includes(',')
+    if (hasTabs || hasCommas) {
+      const consistent = lines.slice(1).every(l => l.includes('\t') || l.includes(','))
+      if (consistent) return 'table'
+    }
+  }
+  
+  // List
+  if (/^[\d\-\*\•]/.test(trimmed) || /^[\d\-\*\•]/.test(lines[0])) {
+    return 'list'
+  }
+  
+  // Code (high density of special chars)
+  const codeChars = (content.match(/[{}()\[\];=]/g) || []).length
+  const codeRatio = codeChars / content.length
+  if (codeRatio > 0.05) return 'code'
+  
+  // Technical (has numbers and units)
+  if (/\d+\s*(px|em|rem|%|ms|s|kb|mb|gb)/i.test(content)) {
+    return 'technical'
+  }
+  
+  // Prose (default - natural language)
+  return 'prose'
+}
+
+/**
+ * Get compression ratio for content.
+ */
+export function getCompressionRatio(content: string, type?: ContentType): { ratio: number; min: number; max: number } {
+  const detectedType = type ?? detectContentType(content)
+  const { min, max, typical } = COMPRESSION_RATIOS[detectedType]
+  
+  // Adjust based on actual content length
+  // Shorter content = higher variance
+  const lengthBonus = content.length < 100 ? 0.5 : 0
+  
+  return {
+    ratio: typical,
+    min: min + lengthBonus,
+    max: max + lengthBonus,
+  }
+}
+
+/**
+ * Estimate tokens with confidence bounds.
+ */
+export function estimateWithBounds(
+  content: string,
+  type?: ContentType,
+): { estimate: number; min: number; max: number } {
+  const { ratio, min: minRatio, max: maxRatio } = getCompressionRatio(content, type)
+  
+  const estimate = roughTokenCountEstimation(content, ratio)
+  const min = roughTokenCountEstimation(content, maxRatio)
+  const max = roughTokenCountEstimation(content, minRatio)
+  
+  return { estimate, min, max }
+}
+
 /**
  * Estimates token count for a Message object by extracting and analyzing its text content.
  * This provides a more reliable estimate than getTokenUsage for messages that may have been compacted.
diff --git a/src/services/tokenModelCompression.test.ts b/src/services/tokenModelCompression.test.ts
new file mode 100644
index 00000000..abfee7c4
--- /dev/null
+++ b/src/services/tokenModelCompression.test.ts
@@ -0,0 +1,100 @@
+import { describe, expect, it } from 'bun:test'
+import {
+  getTokenizerConfig,
+  getBytesPerTokenForModel,
+  detectContentType,
+  getCompressionRatio,
+  estimateWithBounds,
+} from './tokenEstimation.js'
+
+describe('Model Tokenizers', () => {
+  describe('getTokenizerConfig', () => {
+    it('returns config for claude models', () => {
+      const config = getTokenizerConfig('claude-sonnet-4-5-20250514')
+      expect(config.modelFamily).toBe('claude')
+      expect(config.bytesPerToken).toBe(3.5)
+    })
+
+    it('returns config for gpt models', () => {
+      const config = getTokenizerConfig('gpt-4')
+      expect(config.modelFamily).toBe('gpt-4')
+      expect(config.bytesPerToken).toBe(4)
+    })
+
+    it('returns default for unknown models', () => {
+      const config = getTokenizerConfig('unknown-model')
+      expect(config.modelFamily).toBe('unknown')
+      expect(config.bytesPerToken).toBe(4)
+    })
+  })
+
+  describe('getBytesPerTokenForModel', () => {
+    it('returns bytes per token for model', () => {
+      expect(getBytesPerTokenForModel('claude-opus-3-5-20250214')).toBe(3.5)
+      expect(getBytesPerTokenForModel('gpt-4o')).toBe(4)
+      expect(getBytesPerTokenForModel('deepseek-chat')).toBe(3.5)
+      expect(getBytesPerTokenForModel('minimax-M2.7')).toBe(3.2)
+    })
+  })
+})
+
+describe('Content Type Detection', () => {
+  describe('detectContentType', () => {
+    it('detects JSON', () => {
+      expect(detectContentType('{"key": "value"}')).toBe('json')
+      expect(detectContentType('[1, 2, 3]')).toBe('json')
+    })
+
+    it('detects code', () => {
+      expect(detectContentType('function test() { return 1 + 2; }')).toBe('code')
+      expect(detectContentType('const x = () => {}')).toBe('code')
+    })
+
+    it('detects prose', () => {
+      expect(detectContentType('This is a natural language response.')).toBe('prose')
+      expect(detectContentType('Hello world how are you?')).toBe('prose')
+    })
+
+    it('detects code-like technical', () => {
+      // Has both code chars and technical - higher code char ratio wins
+      expect(detectContentType('margin: 10px; padding: 5px;')).toBe('code')
+    })
+
+    it('detects list', () => {
+      expect(detectContentType('- item 1\n- item 2')).toBe('list')
+      expect(detectContentType('1. first\n2. second')).toBe('list')
+    })
+
+    it('detects prose by default', () => {
+      // Single column with newlines = prose
+      expect(detectContentType('a b c\n1 2 3')).toBe('prose')
+    })
+  })
+})
+
+describe('Compression Ratio', () => {
+  describe('getCompressionRatio', () => {
+    it('returns appropriate ratios', () => {
+      expect(getCompressionRatio('{"a":1}').ratio).toBe(2)
+      expect(getCompressionRatio('code here {} []').ratio).toBe(3.5)
+      expect(getCompressionRatio('Hello world').ratio).toBe(4)
+    })
+  })
+
+  describe('estimateWithBounds', () => {
+    it('returns estimate with bounds', () => {
+      const result = estimateWithBounds('Hello world')
+      
+      expect(result.min).toBeLessThanOrEqual(result.estimate)
+      expect(result.max).toBeGreaterThanOrEqual(result.estimate)
+      expect(result.min).toBeLessThan(result.max)
+    })
+
+    it('handles JSON with tighter bounds', () => {
+      const result = estimateWithBounds('{"key": "value"}')
+      
+      // JSON has smaller ratio range
+      expect(result.max).toBeLessThan(10)
+    })
+  })
+})
\ No newline at end of file