diff --git a/CHANGELOG.adoc b/CHANGELOG.adoc
index 8866a010de..e57bae3c37 100644
--- a/CHANGELOG.adoc
+++ b/CHANGELOG.adoc
@@ -6,6 +6,8 @@ This file documents all notable changes to https://github.com/devonfw/IDEasy[IDE
 
 Release with new features and bugfixes:
 
+* https://github.com/devonfw/IDEasy/issues/2286[#2286]: Fix SystemPath.findBinary to search extraPathEntries
+
 
 The full list of changes for this release can be found in https://github.com/devonfw/IDEasy/milestone/49?closed=1[milestone 2026.08.002].
 
diff --git a/cli/src/main/java/com/devonfw/tools/ide/common/SystemPath.java b/cli/src/main/java/com/devonfw/tools/ide/common/SystemPath.java
index 310acc00ba..d3215a5c09 100644
--- a/cli/src/main/java/com/devonfw/tools/ide/common/SystemPath.java
+++ b/cli/src/main/java/com/devonfw/tools/ide/common/SystemPath.java
@@ -284,6 +284,12 @@ public Path findBinary(Path toolPath, Predicate<Path> filter) {
     String fileName = toolPath.getFileName().toString();
 
     if (parent == null) {
+      for (Path path : this.extraPathEntries) {
+        Path binaryPath = findBinaryInOrder(path, fileName);
+        if (binaryPath != null && filter.test(binaryPath)) {
+          return binaryPath;
+        }
+      }
       for (Path path : this.tool2pathMap.values()) {
         Path binaryPath = findBinaryInOrder(path, fileName);
         if (binaryPath != null && filter.test(binaryPath)) {
diff --git a/cli/src/test/java/com/devonfw/tools/ide/common/SystemPathTest.java b/cli/src/test/java/com/devonfw/tools/ide/common/SystemPathTest.java
index a2e9c3853c..2fff021f0f 100644
--- a/cli/src/test/java/com/devonfw/tools/ide/common/SystemPathTest.java
+++ b/cli/src/test/java/com/devonfw/tools/ide/common/SystemPathTest.java
@@ -1,5 +1,7 @@
 package com.devonfw.tools.ide.common;
 
+import java.io.IOException;
+import java.nio.file.Files;
 import java.nio.file.Path;
 import java.util.ArrayList;
 import java.util.List;
@@ -143,6 +145,52 @@ void testFindBinaryFindsNothingWithoutFilter() {
     assertThat(result).isEqualTo(test);
   }
 
+  @Test
+  void testFindBinaryFindsBinaryInExtraPathEntries() throws IOException {
+    // arrange
+    IdeTestContext context = newContext(PROJECT_BASIC);
+    Path binDir = context.getIdeHome().resolve("scratch-bin");
+    Files.createDirectories(binDir);
+    // create a plain binary name (no extension) so it works on both Linux and Windows
+    Path fakeToolFile = binDir.resolve("faketool");
+    Files.writeString(fakeToolFile, "@echo hi");
+
+    // empty PATH and no software folder, so tool2pathMap and paths stay empty
+    SystemPath base = new SystemPath(context, "", null, null, ';', List.of());
+    SystemPath merged = base.withPath(null, List.of(binDir));
+
+    // assert
+    assertThat(merged.toString()).contains(binDir.toString());
+    Path resolved = merged.findBinary(Path.of("faketool"));
+    assertThat(resolved).isNotEqualTo(Path.of("faketool"));
+    assertThat(resolved).isEqualTo(fakeToolFile);
+  }
+
+  @Test
+  void testFindBinaryExtraPathEntriesWinsOverTool2pathMap() throws IOException {
+    // arrange - create two directories, both with a binary named "mytool"
+    // tool2pathMap collects subdirectories of softwarePath, so mytool must be a subdirectory
+    IdeTestContext context = newContext(PROJECT_BASIC);
+    Path toolDir = context.getIdeHome().resolve("software-tool");
+    Files.createDirectories(toolDir);
+    Path mytoolInToolDir = toolDir.resolve("mytool");
+    Files.createDirectories(mytoolInToolDir);
+    Files.writeString(mytoolInToolDir.resolve("mytool"), "tool-version");
+
+    Path extraDir = context.getIdeHome().resolve("extra-path");
+    Files.createDirectories(extraDir);
+    Files.writeString(extraDir.resolve("mytool"), "extra-version");
+
+    // tool2pathMap has "software-tool" (mytool is a subdirectory → registered), extraPathEntries has "extraDir"
+    SystemPath base = new SystemPath(context, "", null, toolDir, ';', List.of());
+    SystemPath merged = base.withPath(null, List.of(extraDir));
+
+    // assert - findBinary should return the one from extraPathEntries, NOT from tool2pathMap
+    Path resolved = merged.findBinary(Path.of("mytool"));
+    assertThat(resolved).isEqualTo(extraDir.resolve("mytool"));
+    assertThat(resolved).isNotEqualTo(mytoolInToolDir.resolve("mytool"));
+  }
+
   @Test
   void testConstructorNormalizesPathEntryWithControlCharactersAndKeepsIt() {
     // arrange