diff --git a/VoiceInk/Services/DictionaryImportExportService.swift b/VoiceInk/Services/DictionaryImportExportService.swift
index ae1407e..20f4415 100644
--- a/VoiceInk/Services/DictionaryImportExportService.swift
+++ b/VoiceInk/Services/DictionaryImportExportService.swift
@@ -27,7 +27,8 @@ class DictionaryImportExportService {
         var wordReplacements: [String: String] = [:]
         let replacementsDescriptor = FetchDescriptor<WordReplacement>()
         if let replacements = try? context.fetch(replacementsDescriptor) {
-            wordReplacements = Dictionary(uniqueKeysWithValues: replacements.map { ($0.originalText, $0.replacementText) })
+            // Use uniquingKeysWith to handle potential duplicates gracefully (keep first occurrence)
+            wordReplacements = Dictionary(replacements.map { ($0.originalText, $0.replacementText) }, uniquingKeysWith: { first, _ in first })
         }
 
         let version = Bundle.main.object(forInfoDictionaryKey: "CFBundleShortVersionString") as? String ?? "1.0.0"
@@ -121,7 +122,6 @@ class DictionaryImportExportService {
                         let importedWords = self.extractWords(from: normalizedImportedKey)
 
                         // Check for conflicts and update existing replacements
-                        var hasConflict = false
                         for existingReplacement in existingReplacements {
                             var existingWords = self.extractWords(from: existingReplacement.originalText)
                             var modified = false
@@ -130,7 +130,6 @@ class DictionaryImportExportService {
                                 if let index = existingWords.firstIndex(where: { $0.lowercased() == importedWord.lowercased() }) {
                                     existingWords.remove(at: index)
                                     modified = true
-                                    hasConflict = true
                                 }
                             }
 
diff --git a/VoiceInk/Services/ImportExportService.swift b/VoiceInk/Services/ImportExportService.swift
index 9bfdad4..386c2bb 100644
--- a/VoiceInk/Services/ImportExportService.swift
+++ b/VoiceInk/Services/ImportExportService.swift
@@ -235,9 +235,34 @@ class ImportExportService {
 
                     // Import word replacements to SwiftData
                     if let replacementsToImport = importedSettings.wordReplacements {
+                        let replacementsDescriptor = FetchDescriptor<WordReplacement>()
+                        let existingReplacements = (try? whisperState.modelContext.fetch(replacementsDescriptor)) ?? []
+
+                        // Build a set of existing replacement keys for duplicate checking
+                        var existingKeysSet = Set<String>()
+                        for existing in existingReplacements {
+                            let tokens = existing.originalText
+                                .split(separator: ",")
+                                .map { $0.trimmingCharacters(in: .whitespacesAndNewlines).lowercased() }
+                                .filter { !$0.isEmpty }
+                            existingKeysSet.formUnion(tokens)
+                        }
+
                         for (original, replacement) in replacementsToImport {
-                            let newReplacement = WordReplacement(originalText: original, replacementText: replacement)
-                            whisperState.modelContext.insert(newReplacement)
+                            let importTokens = original
+                                .split(separator: ",")
+                                .map { $0.trimmingCharacters(in: .whitespacesAndNewlines).lowercased() }
+                                .filter { !$0.isEmpty }
+
+                            // Check if any token already exists
+                            let hasConflict = importTokens.contains { existingKeysSet.contains($0) }
+
+                            if !hasConflict {
+                                let newReplacement = WordReplacement(originalText: original, replacementText: replacement)
+                                whisperState.modelContext.insert(newReplacement)
+                                // Add these tokens to the set to prevent duplicates within the import
+                                existingKeysSet.formUnion(importTokens)
+                            }
                         }
                         try? whisperState.modelContext.save()
                         print("Successfully imported word replacements to SwiftData.")