diff --git a/src/core/operations/ExtractIPAddresses.mjs b/src/core/operations/ExtractIPAddresses.mjs
index 97b52478..b74ec8fe 100644
--- a/src/core/operations/ExtractIPAddresses.mjs
+++ b/src/core/operations/ExtractIPAddresses.mjs
@@ -21,7 +21,7 @@ class ExtractIPAddresses extends Operation {
 
         this.name = "Extract IP addresses";
         this.module = "Regex";
-        this.description = "Extracts all IPv4 and IPv6 addresses.<br><br>Warning: Given a string <code>710.65.0.456</code>, this will match <code>10.65.0.45</code> so always check the original input!";
+        this.description = "Extracts all IPv4 and IPv6 addresses.<br><br>Warning: Given a string <code>1.2.3.4.5.6.7.8</code>, this will match <code>1.2.3.4 and 5.6.7.8</code> so always check the original input!";
         this.inputType = "string";
         this.outputType = "string";
         this.args = [
@@ -65,7 +65,21 @@ class ExtractIPAddresses extends Operation {
      */
     run(input, args) {
         const [includeIpv4, includeIpv6, removeLocal, displayTotal, sort, unique] = args,
-            ipv4 = "(?:(?:\\d|[01]?\\d\\d|2[0-4]\\d|25[0-5])\\.){3}(?:25[0-5]|2[0-4]\\d|[01]?\\d\\d|\\d)(?:\\/\\d{1,2})?",
+
+            // IPv4 decimal groups can have values 0 to 255. To construct a regex the following sub-regex is reused:
+            ipv4DecimalByte = "(?:25[0-5]|2[0-4]\\d|1?[0-9]\\d|\\d)",
+            ipv4OctalByte = "(?:0[1-3]?[0-7]{1,2})",
+
+            // Look behind and ahead will be used to exclude matches with additional decimal digits left and right of IP address
+            lookBehind = "(?<!\\d)",
+            lookAhead = "(?!\\d)",
+
+            // Each variant requires exactly 4 groups with literal . between.
+            ipv4Decimal = "(?:" + lookBehind + ipv4DecimalByte + "\\.){3}" + "(?:" + ipv4DecimalByte + lookAhead + ")",
+            ipv4Octal = "(?:" + lookBehind + ipv4OctalByte + "\\.){3}" + "(?:" + ipv4OctalByte + lookAhead + ")",
+
+            // Then we allow IPv4 addresses to be expressed either entirely in decimal or entirely in Octal
+            ipv4 = "(?:" + ipv4Decimal + "|" + ipv4Octal + ")",
             ipv6 = "((?=.*::)(?!.*::.+::)(::)?([\\dA-F]{1,4}:(:|\\b)|){5}|([\\dA-F]{1,4}:){6})(([\\dA-F]{1,4}((?!\\3)::|:\\b|(?![\\dA-F])))|(?!\\2\\3)){2}";
         let ips  = "";
 
diff --git a/tests/operations/index.mjs b/tests/operations/index.mjs
index 27151c3c..aa3306c5 100644
--- a/tests/operations/index.mjs
+++ b/tests/operations/index.mjs
@@ -65,6 +65,7 @@ import "./tests/ELFInfo.mjs";
 import "./tests/Enigma.mjs";
 import "./tests/ExtractEmailAddresses.mjs";
 import "./tests/ExtractHashes.mjs";
+import "./tests/ExtractIPAddresses.mjs";
 import "./tests/Float.mjs";
 import "./tests/FileTree.mjs";
 import "./tests/FletcherChecksum.mjs";
diff --git a/tests/operations/tests/ExtractIPAddresses.mjs b/tests/operations/tests/ExtractIPAddresses.mjs
new file mode 100644
index 00000000..13922e64
--- /dev/null
+++ b/tests/operations/tests/ExtractIPAddresses.mjs
@@ -0,0 +1,133 @@
+/**
+ * ExtractIPAddresses tests.
+ *
+ * @author gchqdev365 [gchqdev365@outlook.com]
+ * @copyright Crown Copyright 2025
+ * @license Apache-2.0
+ */
+import TestRegister from "../../lib/TestRegister.mjs";
+
+TestRegister.addTests([
+    {
+        name: "ExtractIPAddress All Zeros",
+        input: "0.0.0.0",
+        expectedOutput: "0.0.0.0",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress All 10s",
+        input: "10.10.10.10",
+        expectedOutput: "10.10.10.10",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress All 10s",
+        input: "100.100.100.100",
+        expectedOutput: "100.100.100.100",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress 255s",
+        input: "255.255.255.255",
+        expectedOutput: "255.255.255.255",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress double digits",
+        input: "10.10.10.10 25.25.25.25 99.99.99.99",
+        expectedOutput: "10.10.10.10\n25.25.25.25\n99.99.99.99",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress 256 in middle",
+        input: "255.256.255.255 255.255.256.255",
+        expectedOutput: "",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress 256 at each end",
+        input: "256.255.255.255 255.255.255.256",
+        expectedOutput: "",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress silly example",
+        input: "710.65.0.456",
+        expectedOutput: "",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress longer dotted decimal",
+        input: "1.2.3.4.5.6.7.8",
+        expectedOutput: "1.2.3.4\n5.6.7.8",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress octal valid",
+        input: "01.01.01.01 0123.0123.0123.0123 0377.0377.0377.0377",
+        expectedOutput: "01.01.01.01\n0123.0123.0123.0123\n0377.0377.0377.0377",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+    {
+        name: "ExtractIPAddress octal invalid",
+        input: "0378.01.01.01 03.0377.2.3",
+        expectedOutput: "",
+        recipeConfig: [
+            {
+                "op": "Extract IP addresses",
+                "args": [true, true, false, false, false, false]
+            },
+        ],
+    },
+]);
+