diff --git a/core/vdbe/insn.rs b/core/vdbe/insn.rs
index d8dcb1c86..6a42ba21a 100644
--- a/core/vdbe/insn.rs
+++ b/core/vdbe/insn.rs
@@ -507,7 +507,14 @@ pub fn exec_add(mut lhs: &OwnedValue, mut rhs: &OwnedValue) -> OwnedValue {
         rhs = agg.final_value();
     }
     match (lhs, rhs) {
-        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => OwnedValue::Integer(lhs + rhs),
+        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => {
+            let result = lhs.overflowing_add(*rhs);
+            if result.1 {
+                OwnedValue::Float(*lhs as f64 + *rhs as f64)
+            } else {
+                OwnedValue::Integer(result.0)
+            }
+        }
         (OwnedValue::Float(lhs), OwnedValue::Float(rhs)) => OwnedValue::Float(lhs + rhs),
         (OwnedValue::Float(f), OwnedValue::Integer(i))
         | (OwnedValue::Integer(i), OwnedValue::Float(f)) => OwnedValue::Float(*f + *i as f64),
@@ -531,7 +538,14 @@ pub fn exec_subtract(mut lhs: &OwnedValue, mut rhs: &OwnedValue) -> OwnedValue {
         rhs = agg.final_value();
     }
     match (lhs, rhs) {
-        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => OwnedValue::Integer(lhs - rhs),
+        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => {
+            let result = lhs.overflowing_sub(*rhs);
+            if result.1 {
+                OwnedValue::Float(*lhs as f64 - *rhs as f64)
+            } else {
+                OwnedValue::Integer(result.0)
+            }
+        }
         (OwnedValue::Float(lhs), OwnedValue::Float(rhs)) => OwnedValue::Float(lhs - rhs),
         (OwnedValue::Float(lhs), OwnedValue::Integer(rhs)) => OwnedValue::Float(lhs - *rhs as f64),
         (OwnedValue::Integer(lhs), OwnedValue::Float(rhs)) => OwnedValue::Float(*lhs as f64 - rhs),
@@ -557,7 +571,14 @@ pub fn exec_multiply(mut lhs: &OwnedValue, mut rhs: &OwnedValue) -> OwnedValue {
         rhs = agg.final_value();
     }
     match (lhs, rhs) {
-        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => OwnedValue::Integer(lhs * rhs),
+        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => {
+            let result = lhs.overflowing_mul(*rhs);
+            if result.1 {
+                OwnedValue::Float(*lhs as f64 * *rhs as f64)
+            } else {
+                OwnedValue::Integer(result.0)
+            }
+        }
         (OwnedValue::Float(lhs), OwnedValue::Float(rhs)) => OwnedValue::Float(lhs * rhs),
         (OwnedValue::Integer(i), OwnedValue::Float(f))
         | (OwnedValue::Float(f), OwnedValue::Integer(i)) => OwnedValue::Float(*i as f64 * { *f }),
@@ -583,7 +604,14 @@ pub fn exec_divide(mut lhs: &OwnedValue, mut rhs: &OwnedValue) -> OwnedValue {
     }
     match (lhs, rhs) {
         (_, OwnedValue::Integer(0)) | (_, OwnedValue::Float(0.0)) => OwnedValue::Null,
-        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => OwnedValue::Integer(lhs / rhs),
+        (OwnedValue::Integer(lhs), OwnedValue::Integer(rhs)) => {
+            let result = lhs.overflowing_div(*rhs);
+            if result.1 {
+                OwnedValue::Float(*lhs as f64 / *rhs as f64)
+            } else {
+                OwnedValue::Integer(result.0)
+            }
+        }
         (OwnedValue::Float(lhs), OwnedValue::Float(rhs)) => OwnedValue::Float(lhs / rhs),
         (OwnedValue::Float(lhs), OwnedValue::Integer(rhs)) => OwnedValue::Float(lhs / *rhs as f64),
         (OwnedValue::Integer(lhs), OwnedValue::Float(rhs)) => OwnedValue::Float(*lhs as f64 / rhs),
diff --git a/testing/math.test b/testing/math.test
index 6183bc28b..6188c5a71 100644
--- a/testing/math.test
+++ b/testing/math.test
@@ -6,6 +6,7 @@ source $testdir/tester.tcl
 # Tolerance for floating point comparisons
 # FIXME: When Limbo's floating point presentation matches to SQLite, this could/should be removed
 set tolerance 1e-13
+set overflow_tolerance 5e4
 
 do_execsql_test add-int {
   SELECT 10 + 1
@@ -44,6 +45,19 @@ foreach {testnum lhs rhs ans} {
   do_execsql_test add-text-$testnum "SELECT $lhs + $rhs" $::ans
 }
 
+foreach {testnum lhs rhs ans} {
+   1   '9223372036854775807'   '0'   9223372036854775807 
+   2   '9223372036854775807'   '1'   9.22337203685478e+18
+   3   9223372036854775807      0    9223372036854775807 
+   4   9223372036854775807      1    9.22337203685478e+18
+   5   '-9223372036854775808'  '0'   -9223372036854775808 
+   6   '-9223372036854775808'  '-1'  -9.22337203685478e+18
+   7   -9223372036854775808     0    -9223372036854775808 
+   8   -9223372036854775808     -1   -9.22337203685478e+18
+} {
+  do_execsql_test_tolerance add-overflow-$testnum "SELECT $lhs + $rhs" $::ans $overflow_tolerance
+}
+
 do_execsql_test subtract-int {
   SELECT 10 - 1
 } {9}
@@ -81,6 +95,19 @@ foreach {testnum lhs rhs ans} {
   do_execsql_test subtract-text-$testnum "SELECT $lhs - $rhs" $::ans
 }
 
+foreach {testnum lhs rhs ans} {
+   1   '9223372036854775807'   '0'   9223372036854775807 
+   2   '9223372036854775807'   '-1'   9.22337203685478e+18
+   3   9223372036854775807      0    9223372036854775807 
+   4   9223372036854775807      -1    9.22337203685478e+18
+   5   '-9223372036854775808'  '0'   -9223372036854775808 
+   6   '-9223372036854775808'  '1'  -9.22337203685478e+18
+   7   -9223372036854775808     0    -9223372036854775808 
+   8   -9223372036854775808     1   -9.22337203685478e+18
+} {
+  do_execsql_test_tolerance subtract-overflow-$testnum "SELECT $lhs - $rhs" $::ans $overflow_tolerance
+}
+
 do_execsql_test multiply-int {
   SELECT 10 * 2
 } {20}
@@ -122,6 +149,19 @@ foreach {testnum lhs rhs ans} {
   do_execsql_test multiply-text-$testnum "SELECT $lhs * $rhs" $::ans
 }
 
+foreach {testnum lhs rhs ans} {
+   1   '9223372036854775807'   '1'   9223372036854775807 
+   2   '9223372036854775807'   '2'   1.84467440737096e+19
+   3   9223372036854775807      1    9223372036854775807 
+   4   9223372036854775807      2    1.84467440737096e+19
+   5   '-9223372036854775808'  '1'   -9223372036854775808 
+   6   '-9223372036854775808'  '2'  -1.84467440737096e+19
+   7   -9223372036854775808     1    -9223372036854775808 
+   8   -9223372036854775808     2   -1.84467440737096e+19
+} {
+  do_execsql_test_tolerance multiply-overflow-$testnum "SELECT $lhs * $rhs" $::ans $overflow_tolerance
+}
+
 do_execsql_test divide-int {
   SELECT 10 / 2
 } {5}
@@ -183,6 +223,15 @@ foreach {testnum lhs rhs ans} {
   do_execsql_test divide-text-$testnum "SELECT $lhs / $rhs" $::ans
 }
 
+foreach {testnum lhs rhs ans} {
+   5   '-9223372036854775808'  '0'   {} 
+   6   '-9223372036854775808'  '-1'  9.22337203685478e+18
+   7   -9223372036854775808     0    {}
+   8   -9223372036854775808     -1   9.22337203685478e+18
+} {
+  do_execsql_test_tolerance divide-overflow-$testnum "SELECT $lhs / $rhs" $::ans $overflow_tolerance
+}
+
 do_execsql_test add-agg-int {
   SELECT sum(id) + 10 from products
 } {76}