diff --git a/lua/neotest-java/core/file_checker.lua b/lua/neotest-java/core/file_checker.lua
index 4014cf6..9adfcf6 100644
--- a/lua/neotest-java/core/file_checker.lua
+++ b/lua/neotest-java/core/file_checker.lua
@@ -1,20 +1,37 @@
 local JAVA_TEST_FILE_PATTERNS = require("neotest-java.types.patterns").JAVA_TEST_FILE_PATTERNS
+local root_finder = require("neotest-java.core.root_finder")
+local compatible_path = require("neotest-java.util.compatible_path")
+local ch = require("neotest-java.context_holder")
+local path = require("plenary.path")
 
 local FileChecker = {}
 
+local matcher = function(pattern)
+  return function(dir)
+    return string.find(dir, pattern)
+  end
+end
+
 ---@async
 ---@param file_path string
 ---@return boolean
 function FileChecker.is_test_file(file_path)
-	if string.find(file_path, "/main/") then
-		return false
-	end
-	for _, pattern in ipairs(JAVA_TEST_FILE_PATTERNS) do
-		if string.find(file_path, pattern) then
-			return true
-		end
-	end
-	return false
+  file_path = compatible_path(file_path)
+  print(file_path)
+
+  local root = compatible_path(ch.get_context().root or root_finder.find_root(vim.fn.getcwd(), matcher) or "")
+  print(root)
+
+  local relative_path = path:new(file_path):make_relative(root)
+  if string.find(relative_path, "/main/") then
+    return false
+  end
+  for _, pattern in ipairs(JAVA_TEST_FILE_PATTERNS) do
+    if string.find(relative_path, pattern) then
+      return true
+    end
+  end
+  return false
 end
 
 return FileChecker
diff --git a/tests/core/file_checker_spec.lua b/tests/core/file_checker_spec.lua
index 5005c09..144fcfd 100644
--- a/tests/core/file_checker_spec.lua
+++ b/tests/core/file_checker_spec.lua
@@ -2,37 +2,81 @@ local plugin = require("neotest-java")
 local it = require("nio").tests.it -- async
 
 describe("file_checker", function()
-	it("should return true for test files", function()
-		local test_files = {
-			"src/test/java/neotest/NeotestTest.java",
-			"src/test/java/neotest/RepositoryTests.java",
-			"src/test/java/neotest/NeotestIT.java",
-			"src/test/java/neotest/ProductAceptanceTests.java",
-			"src/test/java/neotest/domain/ProductAceptanceTests.java",
-		}
-
-		for _, file_path in ipairs(test_files) do
-			assert.is_true(plugin.is_test_file(file_path))
-		end
-	end)
-
-	it("should return false for a java non-test file", function()
-		local non_test_files = {
-			"src/test/java/neotest/Configuration.java",
-			"src/test/java/neotest/TestRepository.java",
-			"src/test/java/neotest/Neotest.java",
-		}
-		for _, file_path in ipairs(non_test_files) do
-			assert.is_false(plugin.is_test_file(file_path))
-		end
-	end)
-
-	it("should return false for every class inside main folder", function()
-		local non_test_files = {
-			"src/main/java/neotest/NeotestTest.java",
-		}
-		for _, file_path in ipairs(non_test_files) do
-			assert.is_false(plugin.is_test_file(file_path))
-		end
-	end)
+  it("should return true for test files", function()
+    local test_files = {
+      "src/test/java/neotest/NeotestTest.java",
+      "src/test/java/neotest/RepositoryTests.java",
+      "src/test/java/neotest/NeotestIT.java",
+      "src/test/java/neotest/ProductAceptanceTests.java",
+      "src/test/java/neotest/domain/ProductAceptanceTests.java",
+    }
+
+    for _, file_path in ipairs(test_files) do
+      assert.is_true(plugin.is_test_file(file_path))
+    end
+  end)
+
+  it("should return false for a java non-test file", function()
+    local non_test_files = {
+      "src/test/java/neotest/Configuration.java",
+      "src/test/java/neotest/TestRepository.java",
+      "src/test/java/neotest/Neotest.java",
+    }
+    for _, file_path in ipairs(non_test_files) do
+      assert.is_false(plugin.is_test_file(file_path))
+    end
+  end)
+
+  it("should return false for every class inside main folder", function()
+    local non_test_files = {
+      "src/main/java/neotest/NeotestTest.java",
+    }
+    for _, file_path in ipairs(non_test_files) do
+      assert.is_false(plugin.is_test_file(file_path))
+    end
+  end)
+
+  it("should return true if theres a /main/ outside the root path", function()
+    local ch = require "neotest-java.context_holder"
+    ch.set_root '/absolute_path/main/src'
+    local non_test_files = {
+      "/absolute_path/main/src/java/neotest/NeotestTest.java",
+    }
+    for _, file_path in ipairs(non_test_files) do
+      assert.is_true(plugin.is_test_file(file_path))
+    end
+    ch.set_root ''
+  end)
+
+  it("should return false if theres a /main/ inside the root path in a windows env", function()
+    vim.fn.win64 = {}
+    local ch = require "neotest-java.context_holder"
+    ch.set_root 'C:\\absolute_path\\main\\src'
+
+    local non_test_files = {
+      "C:\\absolute_path\\src\\main\\java\\neotest\\NeotestTest.java",
+    }
+    for _, file_path in ipairs(non_test_files) do
+      assert.is_false(plugin.is_test_file(file_path))
+    end
+
+    ch.set_root ''
+    vim.fn.win64 = nil
+  end)
+
+  it("should return true if theres a /main/ outside the root path in a windows env", function()
+    vim.fn.win64 = {}
+    local ch = require "neotest-java.context_holder"
+    ch.set_root 'C:\\absolute_path\\main\\src'
+
+    local non_test_files = {
+      "C:\\absolute_path\\main\\src\\java\\neotest\\NeotestTest.java",
+    }
+    for _, file_path in ipairs(non_test_files) do
+      assert.is_true(plugin.is_test_file(file_path))
+    end
+
+    ch.set_root ''
+    vim.fn.win64 = nil
+  end)
 end)