diff --git a/apps/web/src/app/create/worksheets/generatePreview.ts b/apps/web/src/app/create/worksheets/generatePreview.ts
index 748bc63e..3289dfec 100644
--- a/apps/web/src/app/create/worksheets/generatePreview.ts
+++ b/apps/web/src/app/create/worksheets/generatePreview.ts
@@ -11,6 +11,7 @@ import {
 import { getSkillById } from './skills'
 import { generateTypstSource } from './typstGenerator'
 import { validateWorksheetConfig } from './validation'
+import { validateProblemSpace } from './utils/validateProblemSpace'
 
 export interface PreviewResult {
   success: boolean
@@ -20,6 +21,7 @@ export interface PreviewResult {
   endPage?: number
   error?: string
   details?: string
+  warnings?: string[] // Added for problem space validation warnings
 }
 
 /**
diff --git a/apps/web/src/app/create/worksheets/utils/validateProblemSpace.ts b/apps/web/src/app/create/worksheets/utils/validateProblemSpace.ts
new file mode 100644
index 00000000..a1371dac
--- /dev/null
+++ b/apps/web/src/app/create/worksheets/utils/validateProblemSpace.ts
@@ -0,0 +1,150 @@
+/**
+ * Validate that worksheet configuration has enough problem space to avoid excessive duplicates
+ */
+
+export interface ProblemSpaceValidation {
+  isValid: boolean
+  warnings: string[]
+  estimatedUniqueProblems: number
+  requestedProblems: number
+  duplicateRisk: 'none' | 'low' | 'medium' | 'high' | 'extreme'
+}
+
+/**
+ * Estimate the maximum unique problems possible given constraints
+ */
+function estimateUniqueProblemSpace(
+  digitRange: { min: number; max: number },
+  pAnyRegroup: number,
+  operator: 'addition' | 'subtraction'
+): number {
+  const { min: minDigits, max: maxDigits } = digitRange
+
+  // Calculate approximate number space for each digit count
+  let totalSpace = 0
+  for (let digits = minDigits; digits <= maxDigits; digits++) {
+    // For N-digit numbers: 9 * 10^(N-1) possibilities (e.g., 2-digit = 90 numbers from 10-99)
+    const numbersPerDigitCount = digits === 1 ? 9 : 9 * Math.pow(10, digits - 1)
+
+    if (operator === 'addition') {
+      // Addition: a + b where both are in the digit range
+      // Rough estimate: numbersPerDigitCount^2 / 2 (since a+b = b+a, but we count both)
+      // Then filter by regrouping probability
+      const pairsForDigits = numbersPerDigitCount * numbersPerDigitCount
+
+      // If pAnyRegroup is high, only a fraction of pairs will work
+      // Regrouping is more common with larger digits, so this is approximate
+      const regroupFactor = pAnyRegroup > 0.8 ? 0.3 : pAnyRegroup > 0.5 ? 0.5 : 0.7
+
+      totalSpace += pairsForDigits * regroupFactor
+    } else {
+      // Subtraction: minuend - subtrahend where minuend > subtrahend
+      // About half the pairs (where minuend > subtrahend)
+      const pairsForDigits = (numbersPerDigitCount * numbersPerDigitCount) / 2
+
+      // Borrowing constraints reduce space similarly
+      const borrowFactor = pAnyRegroup > 0.8 ? 0.3 : pAnyRegroup > 0.5 ? 0.5 : 0.7
+
+      totalSpace += pairsForDigits * borrowFactor
+    }
+  }
+
+  return Math.floor(totalSpace)
+}
+
+/**
+ * Validate worksheet configuration for duplicate risk
+ * Returns warnings if configuration will likely produce many duplicates
+ */
+export function validateProblemSpace(
+  problemsPerPage: number,
+  pages: number,
+  digitRange: { min: number; max: number },
+  pAnyStart: number,
+  operator: 'addition' | 'subtraction' | 'mixed'
+): ProblemSpaceValidation {
+  const requestedProblems = problemsPerPage * pages
+  const warnings: string[] = []
+
+  // For mixed mode, assume half of each
+  let estimatedSpace: number
+  if (operator === 'mixed') {
+    const addSpace = estimateUniqueProblemSpace(digitRange, pAnyStart, 'addition')
+    const subSpace = estimateUniqueProblemSpace(digitRange, pAnyStart, 'subtraction')
+    estimatedSpace = addSpace + subSpace
+  } else {
+    estimatedSpace = estimateUniqueProblemSpace(digitRange, pAnyStart, operator)
+  }
+
+  // Calculate duplicate risk
+  const ratio = requestedProblems / estimatedSpace
+  let duplicateRisk: 'none' | 'low' | 'medium' | 'high' | 'extreme'
+
+  if (ratio < 0.3) {
+    duplicateRisk = 'none'
+  } else if (ratio < 0.5) {
+    duplicateRisk = 'low'
+    warnings.push(
+      `You're requesting ${requestedProblems} problems, but only ~${Math.floor(estimatedSpace)} unique problems are possible with these constraints. Some duplicates may occur.`
+    )
+  } else if (ratio < 0.8) {
+    duplicateRisk = 'medium'
+    warnings.push(
+      `Warning: Only ~${Math.floor(estimatedSpace)} unique problems possible, but you're requesting ${requestedProblems}. Expect moderate duplicates.`
+    )
+    warnings.push(
+      `Suggestion: Reduce pages to ${Math.floor(estimatedSpace * 0.5 / problemsPerPage)} or increase digit range to ${digitRange.max + 1}`
+    )
+  } else if (ratio < 1.5) {
+    duplicateRisk = 'high'
+    warnings.push(
+      `High duplicate risk! Only ~${Math.floor(estimatedSpace)} unique problems possible for ${requestedProblems} requested.`
+    )
+    warnings.push(
+      `Recommendations:\n` +
+        `  • Reduce to ${Math.floor(estimatedSpace * 0.5 / problemsPerPage)} pages (50% of available space)\n` +
+        `  • Increase digit range to ${digitRange.max + 1}-${digitRange.max + 1}\n` +
+        `  • Lower regrouping probability from ${Math.round(pAnyStart * 100)}% to 50%`
+    )
+  } else {
+    duplicateRisk = 'extreme'
+    warnings.push(
+      `Extreme duplicate risk! Requesting ${requestedProblems} problems but only ~${Math.floor(estimatedSpace)} unique problems exist.`
+    )
+    warnings.push(
+      `This configuration will produce mostly duplicate problems.`
+    )
+    warnings.push(
+      `Strong recommendations:\n` +
+        `  • Reduce to ${Math.floor(estimatedSpace * 0.5 / problemsPerPage)} pages maximum\n` +
+        `  • OR increase digit range from ${digitRange.min}-${digitRange.max} to ${digitRange.min}-${digitRange.max + 1}\n` +
+        `  • OR reduce regrouping requirement from ${Math.round(pAnyStart * 100)}%`
+    )
+  }
+
+  // Special case: single digit with high regrouping is extremely constrained
+  if (digitRange.min === 1 && digitRange.max === 1 && pAnyStart > 0.8 && requestedProblems > 50) {
+    warnings.unshift(
+      `Single-digit problems (1-9) with ${Math.round(pAnyStart * 100)}% regrouping have very few unique combinations!`
+    )
+  }
+
+  return {
+    isValid: duplicateRisk !== 'extreme',
+    warnings,
+    estimatedUniqueProblems: Math.floor(estimatedSpace),
+    requestedProblems,
+    duplicateRisk,
+  }
+}
+
+/**
+ * Format validation result for display to user
+ */
+export function formatValidationWarnings(validation: ProblemSpaceValidation): string {
+  if (validation.warnings.length === 0) {
+    return ''
+  }
+
+  return validation.warnings.join('\n\n')
+}