diff --git a/config/http_config.go b/config/http_config.go
index 689ea627..88457375 100644
--- a/config/http_config.go
+++ b/config/http_config.go
@@ -325,7 +325,7 @@ func LoadHTTPConfigFile(filename string) (*HTTPClientConfig, []byte, error) {
 	if err != nil {
 		return nil, nil, err
 	}
-	cfg.SetDirectory(filepath.Dir(filepath.Dir(filename)))
+	cfg.SetDirectory(filepath.Dir(filename))
 	return cfg, content, nil
 }
 
diff --git a/config/http_config_test.go b/config/http_config_test.go
index 708e993b..4d61ae12 100644
--- a/config/http_config_test.go
+++ b/config/http_config_test.go
@@ -2720,3 +2720,32 @@ func TestMultipleHeaders(t *testing.T) {
 	_, err = client.Get(ts.URL)
 	require.NoErrorf(t, err, "can't fetch URL: %v", err)
 }
+
+// TestLoadHTTPConfigFileResolvesPathsRelativeToConfigFile ensures that relative
+// file paths inside a config loaded with LoadHTTPConfigFile are resolved
+// relative to the directory containing the config file, as documented by the
+// SetDirectory contract.
+func TestLoadHTTPConfigFileResolvesPathsRelativeToConfigFile(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		require.Equal(t, "header-value", r.Header.Get("X-Test"))
+		w.WriteHeader(http.StatusNoContent)
+	}))
+	t.Cleanup(ts.Close)
+
+	dir := t.TempDir()
+	require.NoError(t, os.WriteFile(filepath.Join(dir, "header-value"), []byte("header-value\n"), 0o644))
+	require.NoError(t, os.WriteFile(filepath.Join(dir, "http.yml"), []byte(`http_headers:
+  X-Test:
+    files: [header-value]
+`), 0o644))
+
+	cfg, _, err := LoadHTTPConfigFile(filepath.Join(dir, "http.yml"))
+	require.NoErrorf(t, err, "Error loading HTTP client config: %v", err)
+	require.Equal(t, filepath.Join(dir, "header-value"), cfg.HTTPHeaders.Headers["X-Test"].Files[0])
+
+	client, err := NewClientFromConfig(*cfg, "test")
+	require.NoErrorf(t, err, "Error creating HTTP Client: %v", err)
+
+	_, err = client.Get(ts.URL)
+	require.NoErrorf(t, err, "can't fetch URL: %v", err)
+}
diff --git a/config/testdata/http.conf.basic-auth.bad-username.yaml b/config/testdata/http.conf.basic-auth.bad-username.yaml
index bfb911b8..7b2f74ea 100644
--- a/config/testdata/http.conf.basic-auth.bad-username.yaml
+++ b/config/testdata/http.conf.basic-auth.bad-username.yaml
@@ -1,4 +1,4 @@
 basic_auth:
   username: user
-  username_file: testdata/basic-auth-username
+  username_file: basic-auth-username
   password: foo
\ No newline at end of file
diff --git a/config/testdata/http.conf.basic-auth.good.yaml b/config/testdata/http.conf.basic-auth.good.yaml
index 5e7aa41f..8b96a413 100644
--- a/config/testdata/http.conf.basic-auth.good.yaml
+++ b/config/testdata/http.conf.basic-auth.good.yaml
@@ -1,3 +1,3 @@
 basic_auth:
   username: user
-  password_file: testdata/basic-auth-password
+  password_file: basic-auth-password
diff --git a/config/testdata/http.conf.basic-auth.too-much.bad.yaml b/config/testdata/http.conf.basic-auth.too-much.bad.yaml
index 7cfb9220..f282bf7c 100644
--- a/config/testdata/http.conf.basic-auth.too-much.bad.yaml
+++ b/config/testdata/http.conf.basic-auth.too-much.bad.yaml
@@ -1,4 +1,4 @@
 basic_auth:
   username: user
   password: foo
-  password_file: testdata/basic-auth-password
+  password_file: basic-auth-password
diff --git a/config/testdata/http.conf.basic-auth.username-file.good.yaml b/config/testdata/http.conf.basic-auth.username-file.good.yaml
index 24c3c3cb..102dbe77 100644
--- a/config/testdata/http.conf.basic-auth.username-file.good.yaml
+++ b/config/testdata/http.conf.basic-auth.username-file.good.yaml
@@ -1,3 +1,3 @@
 basic_auth:
-  username_file: testdata/basic-auth-username
-  password_file: testdata/basic-auth-password
\ No newline at end of file
+  username_file: basic-auth-username
+  password_file: basic-auth-password
\ No newline at end of file
diff --git a/config/testdata/http.conf.headers-multiple.good.yaml b/config/testdata/http.conf.headers-multiple.good.yaml
index f9dcdc05..b8e6d7e0 100644
--- a/config/testdata/http.conf.headers-multiple.good.yaml
+++ b/config/testdata/http.conf.headers-multiple.good.yaml
@@ -5,4 +5,4 @@ http_headers:
     values: [value2a]
     secrets: [value2b, value2c]
   three:
-    files: [testdata/headers-file-a, testdata/headers-file-b, testdata/headers-file-c]
+    files: [headers-file-a, headers-file-b, headers-file-c]
diff --git a/config/testdata/http.conf.headers.good.yaml b/config/testdata/http.conf.headers.good.yaml
index f8a02364..5b46cf7f 100644
--- a/config/testdata/http.conf.headers.good.yaml
+++ b/config/testdata/http.conf.headers.good.yaml
@@ -4,4 +4,4 @@ http_headers:
   two:
     secrets: [value2]
   three:
-    files: [testdata/headers-file]
+    files: [headers-file]