diff --git a/src/TrueCV.Infrastructure/Jobs/ProcessCVCheckJob.cs b/src/TrueCV.Infrastructure/Jobs/ProcessCVCheckJob.cs
index 70c517c..cfc6cf5 100644
--- a/src/TrueCV.Infrastructure/Jobs/ProcessCVCheckJob.cs
+++ b/src/TrueCV.Infrastructure/Jobs/ProcessCVCheckJob.cs
@@ -261,26 +261,48 @@ public sealed class ProcessCVCheckJob
         var score = BaseScore;
         var flags = new List<FlagResult>();
 
-        // Penalty for unverified companies
-        foreach (var verification in verifications.Where(v => !v.IsVerified))
+        // Penalty for unverified companies (deduplicated by company name)
+        var unverifiedByCompany = verifications
+            .Where(v => !v.IsVerified)
+            .GroupBy(v => v.ClaimedCompany, StringComparer.OrdinalIgnoreCase)
+            .ToList();
+
+        foreach (var companyGroup in unverifiedByCompany)
         {
             score -= UnverifiedCompanyPenalty;
+            var firstInstance = companyGroup.First();
+            var instanceCount = companyGroup.Count();
+
+            var description = instanceCount > 1
+                ? $"Could not verify employment at '{firstInstance.ClaimedCompany}' ({instanceCount} roles). {firstInstance.VerificationNotes}"
+                : $"Could not verify employment at '{firstInstance.ClaimedCompany}'. {firstInstance.VerificationNotes}";
 
             flags.Add(new FlagResult
             {
                 Category = FlagCategory.Employment.ToString(),
                 Severity = FlagSeverity.Warning.ToString(),
                 Title = "Unverified Company",
-                Description = $"Could not verify employment at '{verification.ClaimedCompany}'. {verification.VerificationNotes}",
+                Description = description,
                 ScoreImpact = -UnverifiedCompanyPenalty
             });
         }
 
         // Process company verification flags (incorporation date, dissolution, dormant, etc.)
+        // Deduplicate by (company, flag type) to avoid penalizing same issue multiple times
+        var processedCompanyFlags = new HashSet<(string Company, string FlagType)>(
+            new CompanyFlagComparer());
+
         foreach (var verification in verifications.Where(v => v.Flags.Count > 0))
         {
             foreach (var companyFlag in verification.Flags)
             {
+                var key = (verification.ClaimedCompany, companyFlag.Type);
+                if (!processedCompanyFlags.Add(key))
+                {
+                    // Already processed this flag for this company, skip
+                    continue;
+                }
+
                 var penalty = Math.Abs(companyFlag.ScoreImpact);
                 score -= penalty;
 
@@ -660,4 +682,24 @@ public sealed class ProcessCVCheckJob
         // Level 1: Junior / Entry-level
         return 1;
     }
+
+    /// <summary>
+    /// Comparer for deduplicating company flags by (company name, flag type).
+    /// Uses case-insensitive comparison for company names.
+    /// </summary>
+    private sealed class CompanyFlagComparer : IEqualityComparer<(string Company, string FlagType)>
+    {
+        public bool Equals((string Company, string FlagType) x, (string Company, string FlagType) y)
+        {
+            return string.Equals(x.Company, y.Company, StringComparison.OrdinalIgnoreCase) &&
+                   string.Equals(x.FlagType, y.FlagType, StringComparison.OrdinalIgnoreCase);
+        }
+
+        public int GetHashCode((string Company, string FlagType) obj)
+        {
+            return HashCode.Combine(
+                obj.Company?.ToUpperInvariant() ?? "",
+                obj.FlagType?.ToUpperInvariant() ?? "");
+        }
+    }
 }