diff --git a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/ExtendedCalculatorParserTests.cs b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/ExtendedCalculatorParserTests.cs
index d62fbf668f..b13072021b 100644
--- a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/ExtendedCalculatorParserTests.cs
+++ b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/ExtendedCalculatorParserTests.cs
@@ -197,6 +197,8 @@ namespace Microsoft.PowerToys.Run.Plugin.Calculator.UnitTests
         [DataRow("randi(0.5)", true)]
         [DataRow("rand()", true)]
         [DataRow("rand(0.5)", false)]
+        [DataRow("0X78AD+0o123", true)]
+        [DataRow("0o9", false)]
         public void InputValid_TestValid_WhenCalled(string input, bool valid)
         {
             // Act
@@ -233,7 +235,8 @@ namespace Microsoft.PowerToys.Run.Plugin.Calculator.UnitTests
                new object[] { "abs(-2)", 2M },
                new object[] { "abs(2)", 2M },
                new object[] { "0+(1*2)/(0+1)", 2M }, // Validate that division by "(0+1)" is not interpret as division by zero.
-               new object[] { "0+(1*2)/0.5", 4M }, // Validate that division by  number with decimal digits is not interpret as division by zero.
+               new object[] { "0+(1*2)/0.5", 4M }, // Validate that division by number with decimal digits is not interpret as division by zero.
+               new object[] { "0+(1*2)/0o004", 0.5M }, // Validate that division by an octal number with zeroes is not treated as division by zero.
            };
 
         [DataTestMethod]
diff --git a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/QueryTests.cs b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/QueryTests.cs
index 6f858caf03..75e20e8795 100644
--- a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/QueryTests.cs
+++ b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator.UnitTest/QueryTests.cs
@@ -41,6 +41,8 @@ namespace Microsoft.PowerToys.Run.Plugin.Calculator.UnitTests
         [DataRow("=5 / 0", "Expression contains division by zero")]
         [DataRow("10+(8*9)/0+7", "Expression contains division by zero")]
         [DataRow("10+(8*9)/0*7", "Expression contains division by zero")]
+        [DataRow("10+(8*9)/0x00", "Expression contains division by zero")]
+        [DataRow("10+(8*9)/0b0", "Expression contains division by zero")]
         public void ErrorResultOnInvalidKeywordQuery(string typedString, string expectedResult)
         {
             Query expectedQuery = new(typedString, "=");
diff --git a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateEngine.cs b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateEngine.cs
index 3aef7ba254..815a52d8b0 100644
--- a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateEngine.cs
+++ b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateEngine.cs
@@ -37,8 +37,8 @@ namespace Microsoft.PowerToys.Run.Plugin.Calculator
             }
 
             // check for division by zero
-            // We check if the string contains a slash followed by space (optional) and zero. Whereas the zero must not be followed by a dot, comma, or 'x'/'X' as these indicate a number with decimal digits or a hexadecimal value respectively. The zero must also not be followed by other digits.
-            if (new Regex("\\/\\s*0(?![,\\.0-9xX])").Match(input).Success)
+            // We check if the string contains a slash followed by space (optional) and zero. Whereas the zero must not be followed by a dot, comma, 'b', 'o' or 'x' as these indicate a number with decimal digits or a binary/octal/hexadecimal value respectively. The zero must also not be followed by other digits.
+            if (new Regex("\\/\\s*0(?!(?:[,\\.0-9]|[box]0*[1-9a-f]))", RegexOptions.IgnoreCase).Match(input).Success)
             {
                 error = Properties.Resources.wox_plugin_calculator_division_by_zero;
                 return default;
diff --git a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateHelper.cs b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateHelper.cs
index 59bc414bda..436591e3b3 100644
--- a/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateHelper.cs
+++ b/src/modules/launcher/Plugins/Microsoft.PowerToys.Run.Plugin.Calculator/CalculateHelper.cs
@@ -21,7 +21,7 @@ namespace Microsoft.PowerToys.Run.Plugin.Calculator
             @"pi|" +
             @"==|~=|&&|\|\||" +
             @"((-?(\d+(\.\d*)?)|-?(\.\d+))[Ee](-?\d+))|" + /* expression from CheckScientificNotation between parenthesis */
-            @"e|[0-9]|0x[0-9a-fA-F]+|0b[01]+|[\+\-\*\/\^\., ""]|[\(\)\|\!\[\]]" +
+            @"e|[0-9]|0[xX][0-9a-fA-F]+|0[bB][01]+|0[oO][0-7]+|[\+\-\*\/\^\., ""]|[\(\)\|\!\[\]]" +
             @")+$",
             RegexOptions.Compiled);