diff --git a/src/test/data/script_tests.json b/src/test/data/script_tests.json
--- a/src/test/data/script_tests.json
+++ b/src/test/data/script_tests.json
@@ -988,33 +988,62 @@
 ["1 -1", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
 ["-1 1", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
 ["-1 -1", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["2 2", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["2 -2", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["-2 2", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["-2 -2", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["0 1", "DIV 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["1 0", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "DIV_BY_ZERO", "DIV, divide by zero"],
-["3 2", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Round towards zero"],
-["3 -2", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Round towards zero"],
+["28 21", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Round towards zero"],
+["12 -7", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Round towards zero"],
+["-32 29", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Round towards zero"],
+["-42 -27", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Round towards zero"],
+["0 123", "DIV 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["511 0", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "DIV_BY_ZERO", "DIV, divide by zero"],
 ["1 1", "DIV DEPTH 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Stack depth correct"],
 ["1", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "INVALID_STACK_OPERATION", "Not enough operands"],
 ["0", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "INVALID_STACK_OPERATION", "Not enough operands"],
-["1 1", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["2147483647 1", "DIV 2147483647 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["1 2147483647", "DIV 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["2147483647 2147483647", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 1", "DIV -2147483647 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-1 2147483647", "DIV 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 2147483647", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["2147483647 -1", "DIV -2147483647 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["1 -2147483647", "DIV 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["2147483647 -2147483647", "DIV -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 -1", "DIV 2147483647 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-1 -2147483647", "DIV 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 -2147483647", "DIV 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
 ["2147483648 1", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
 ["1 2147483648", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
+["-2147483648 1", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
+["1 -2147483648", "DIV", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
 
 ["MOD"],
 ["1 1", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["7 -3", "MOD 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["-7 3", "MOD -1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
-["10 3", "MOD 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["-1 1", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["1 -1", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["-1 -1", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["82 23", "MOD 13 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["8 -3", "MOD 2 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["-71 13", "MOD -6 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
+["-110 -31", "MOD -17 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
 ["0 1", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK"],
 ["1 0", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "MOD_BY_ZERO", "MOD, modulo by zero"],
 ["1 1", "MOD DEPTH 1 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Stack depth correct"],
 ["1", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "INVALID_STACK_OPERATION", "Not enough operands"],
 ["0", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "INVALID_STACK_OPERATION", "Not enough operands"],
+["2147483647 123", "MOD 79 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["123 2147483647", "MOD 123 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["2147483647 2147483647", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 123", "MOD -79 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-123 2147483647", "MOD -123 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 2147483647", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["2147483647 -123", "MOD 79 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["123 -2147483647", "MOD 123 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["2147483647 -2147483647", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 -123", "MOD -79 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-123 -2147483647", "MOD -123 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
+["-2147483647 -2147483647", "MOD 0 EQUAL", "P2SH,STRICTENC,MONOLITH_OPCODES", "OK", "Check boundary condition"],
 ["2147483648 1", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
 ["1 2147483648", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
+["-2147483648 1", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
+["1 -2147483648", "MOD", "P2SH,STRICTENC,MONOLITH_OPCODES", "UNKNOWN_ERROR", "We cannot do math on 5-byte integers"],
 
 ["EQUAL"],
 ["", "EQUAL NOT", "P2SH,STRICTENC", "INVALID_STACK_OPERATION", "EQUAL must error when there are no stack items"],