diff --git a/cli/cliui/table.go b/cli/cliui/table.go
index cd26c43182..cd417641f6 100644
--- a/cli/cliui/table.go
+++ b/cli/cliui/table.go
@@ -158,6 +158,10 @@ func DisplayTable(out any, sort string, filterColumns []string) (string, error)
 				if val != nil {
 					v = val.Format(time.RFC3339)
 				}
+			case *int64:
+				if val != nil {
+					v = *val
+				}
 			case fmt.Stringer:
 				if val != nil {
 					v = val.String()
diff --git a/enterprise/coderd/license/license.go b/enterprise/coderd/license/license.go
index 213d5dafb8..55a62eee17 100644
--- a/enterprise/coderd/license/license.go
+++ b/enterprise/coderd/license/license.go
@@ -60,17 +60,17 @@ func Entitlements(ctx context.Context, db database.Store, logger slog.Logger, ke
 			entitlement = codersdk.EntitlementGracePeriod
 		}
 		if claims.Features.UserLimit > 0 {
+			limit := claims.Features.UserLimit
+			priorLimit := entitlements.Features[codersdk.FeatureUserLimit]
+			if priorLimit.Limit != nil && *priorLimit.Limit > limit {
+				limit = *priorLimit.Limit
+			}
 			entitlements.Features[codersdk.FeatureUserLimit] = codersdk.Feature{
 				Enabled:     true,
 				Entitlement: entitlement,
-				Limit:       &claims.Features.UserLimit,
+				Limit:       &limit,
 				Actual:      &activeUserCount,
 			}
-			if activeUserCount > claims.Features.UserLimit {
-				entitlements.Warnings = append(entitlements.Warnings, fmt.Sprintf(
-					"Your deployment has %d active users but is only licensed for %d.",
-					activeUserCount, claims.Features.UserLimit))
-			}
 		}
 		if claims.Features.AuditLog > 0 {
 			entitlements.Features[codersdk.FeatureAuditLog] = codersdk.Feature{
@@ -114,6 +114,13 @@ func Entitlements(ctx context.Context, db database.Store, logger slog.Logger, ke
 	}
 
 	if entitlements.HasLicense {
+		userLimit := entitlements.Features[codersdk.FeatureUserLimit].Limit
+		if userLimit != nil && activeUserCount > *userLimit {
+			entitlements.Warnings = append(entitlements.Warnings, fmt.Sprintf(
+				"Your deployment has %d active users but is only licensed for %d.",
+				activeUserCount, *userLimit))
+		}
+
 		for _, featureName := range codersdk.FeatureNames {
 			// The user limit has it's own warnings!
 			if featureName == codersdk.FeatureUserLimit {
diff --git a/enterprise/coderd/license/license_test.go b/enterprise/coderd/license/license_test.go
index 04141718e6..85958fbf4f 100644
--- a/enterprise/coderd/license/license_test.go
+++ b/enterprise/coderd/license/license_test.go
@@ -141,6 +141,28 @@ func TestEntitlements(t *testing.T) {
 		require.True(t, entitlements.HasLicense)
 		require.Contains(t, entitlements.Warnings, "Your deployment has 2 active users but is only licensed for 1.")
 	})
+	t.Run("MaximizeUserLimit", func(t *testing.T) {
+		t.Parallel()
+		db := databasefake.New()
+		db.InsertUser(context.Background(), database.InsertUserParams{})
+		db.InsertUser(context.Background(), database.InsertUserParams{})
+		db.InsertLicense(context.Background(), database.InsertLicenseParams{
+			JWT: coderdenttest.GenerateLicense(t, coderdenttest.LicenseOptions{
+				UserLimit: 10,
+			}),
+			Exp: time.Now().Add(time.Hour),
+		})
+		db.InsertLicense(context.Background(), database.InsertLicenseParams{
+			JWT: coderdenttest.GenerateLicense(t, coderdenttest.LicenseOptions{
+				UserLimit: 1,
+			}),
+			Exp: time.Now().Add(time.Hour),
+		})
+		entitlements, err := license.Entitlements(context.Background(), db, slog.Logger{}, coderdenttest.Keys, map[string]bool{})
+		require.NoError(t, err)
+		require.True(t, entitlements.HasLicense)
+		require.Empty(t, entitlements.Warnings)
+	})
 	t.Run("MultipleLicenseEnabled", func(t *testing.T) {
 		t.Parallel()
 		db := databasefake.New()