diff --git a/CHANGES.md b/CHANGES.md
index 191bff9..859a062 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -74,11 +74,3 @@ The change was made for two reasons:
 
 * Doorstop does not need to pass any arguments anymore. Instead, Doorstop passes all the information via environment variables.
 * CoreCLR does not support easy method searching using wildcards yet.
-
-## *Possibly* breaking: `target_assembly` directory is now always added to mono search path
-
-In UnityDoorstop 3.x, the tool only loaded the `target_assembly` and left any other assembly resolving to the target assembly code.
-**Starting Doorstop 4, `target_assembly`'s parent directory is set to mono DLL search path.**
-
-This means that any additional assemblies that are placed into the same directory as `target_assembly` will receive priority during assembly resolving.
-Note that this option for now only affects UnityMono as there is no similar search path priority available via current CoreCLR C hosting API.
\ No newline at end of file
diff --git a/assets/nix/run.sh b/assets/nix/run.sh
index 257fb00..ab24a52 100755
--- a/assets/nix/run.sh
+++ b/assets/nix/run.sh
@@ -36,6 +36,7 @@ ignore_disable_switch="0"
 # (e.g. mscorlib is stripped in original game)
 # This option causes Mono to seek mscorlib and core libraries from a different folder before Managed
 # Original Managed folder is added as a secondary folder in the search path
+# To specify multiple paths, separate them with colons (:)
 dll_search_path_override=""
 
 # If 1, Mono debugger server will be enabled
diff --git a/assets/windows/doorstop_config.ini b/assets/windows/doorstop_config.ini
index 4c2a493..4803878 100644
--- a/assets/windows/doorstop_config.ini
+++ b/assets/windows/doorstop_config.ini
@@ -24,6 +24,7 @@ ignore_disable_switch=false
 # (e.g. mscorlib is stripped in original game)
 # This option causes Mono to seek mscorlib and core libraries from a different folder before Managed
 # Original Managed folder is added as a secondary folder in the search path
+# To specify multiple paths, separate them with semicolons (;)
 dll_search_path_override=
 
 # If true, Mono debugger server will be enabled
diff --git a/src/bootstrap.c b/src/bootstrap.c
index 6cc60e4..c38790b 100644
--- a/src/bootstrap.c
+++ b/src/bootstrap.c
@@ -134,27 +134,65 @@ void *init_mono(const char *root_domain_name, const char *runtime_version) {
     LOG("Overriding mono DLL search path");
 
     size_t mono_search_path_len = strlen(root_dir) + 1;
-    char_t *target_path_full = get_full_path(config.target_assembly);
-    char_t *target_path_folder = get_folder_name(target_path_full);
-    mono_search_path_len += strlen(target_path_folder) + 1;
-    LOG("Adding %s to mono search path", target_path_folder);
 
     char_t *override_dir_full = NULL;
-    bool_t has_override = config.mono_dll_search_path_override &&
-                          strlen(config.mono_dll_search_path_override);
+    char_t *config_path_value = config.mono_dll_search_path_override;
+    bool_t has_override = config_path_value && strlen(config_path_value);
     if (has_override) {
-        override_dir_full = get_full_path(config.mono_dll_search_path_override);
+        size_t path_start = 0;
+        override_dir_full = calloc(MAX_PATH, sizeof(char_t));
+        memset(override_dir_full, 0, MAX_PATH * sizeof(char_t));
+
+        bool_t found_path = FALSE;
+        for (size_t i = 0; i <= strlen(config_path_value); i++) {
+            char_t current_char = config_path_value[i];
+            if (current_char == *PATH_SEP || current_char == 0) {
+                if (i <= path_start) {
+                    path_start++;
+                    continue;
+                }
+
+                size_t path_len = i - path_start;
+                char_t *path = calloc(path_len + 1, sizeof(char_t));
+                strncpy(path, config_path_value + path_start, path_len);
+                path[path_len] = 0;
+
+                char_t *full_path = get_full_path(path);
+
+                if (strlen(override_dir_full) + strlen(full_path) + 2 >
+                    MAX_PATH) {
+                    LOG("Ignoring this root path because its absolute version "
+                        "is too long: %s",
+                        full_path);
+                    free(path);
+                    free(full_path);
+                    path_start = i + 1;
+                    continue;
+                }
+
+                if (found_path) {
+                    strcat(override_dir_full, PATH_SEP);
+                }
+
+                strcat(override_dir_full, full_path);
+                LOG("Adding root path: %s", full_path);
+
+                free(path);
+                free(full_path);
+
+                found_path = TRUE;
+                path_start = i + 1;
+            }
+        }
+
         mono_search_path_len += strlen(override_dir_full) + 1;
-        LOG("Adding root path: %s", override_dir_full);
     }
 
     char_t *mono_search_path = calloc(mono_search_path_len + 1, sizeof(char_t));
-    if (has_override) {
+    if (override_dir_full && strlen(override_dir_full)) {
         strcat(mono_search_path, override_dir_full);
         strcat(mono_search_path, PATH_SEP);
     }
-    strcat(mono_search_path, target_path_folder);
-    strcat(mono_search_path, PATH_SEP);
     strcat(mono_search_path, root_dir);
 
     LOG("Mono search path: %s", mono_search_path);
@@ -166,8 +204,6 @@ void *init_mono(const char *root_domain_name, const char *runtime_version) {
     if (override_dir_full) {
         free(override_dir_full);
     }
-    free(target_path_full);
-    free(target_path_folder);
 
     hook_mono_jit_parse_options(0, NULL);
 
diff --git a/src/nix/config.c b/src/nix/config.c
index f6d0444..afd8b8e 100644
--- a/src/nix/config.c
+++ b/src/nix/config.c
@@ -37,8 +37,8 @@ void load_config() {
     try_get_env("DOORSTOP_MONO_DEBUG_ADDRESS", TEXT("127.0.0.1:10000"),
                 &config.mono_debug_address);
     get_env_path("DOORSTOP_TARGET_ASSEMBLY", &config.target_assembly);
-    get_env_path("DOORSTOP_MONO_DLL_SEARCH_PATH_OVERRIDE",
-                 &config.mono_dll_search_path_override);
+    try_get_env("DOORSTOP_MONO_DLL_SEARCH_PATH_OVERRIDE", TEXT(""),
+                &config.mono_dll_search_path_override);
     get_env_path("DOORSTOP_CLR_RUNTIME_CORECLR_PATH",
                  &config.clr_runtime_coreclr_path);
     get_env_path("DOORSTOP_CLR_CORLIB_DIR", &config.clr_corlib_dir);
diff --git a/src/windows/config.c b/src/windows/config.c
index 4babb9d..493230d 100644
--- a/src/windows/config.c
+++ b/src/windows/config.c
@@ -72,9 +72,9 @@ static inline void init_config_file() {
     load_path_file(config_path, TEXT("General"), TEXT("target_assembly"),
                    DEFAULT_TARGET_ASSEMBLY, &config.target_assembly);
 
-    load_path_file(config_path, TEXT("UnityMono"),
-                   TEXT("dll_search_path_override"), NULL,
-                   &config.mono_dll_search_path_override);
+    load_str_file(config_path, TEXT("UnityMono"),
+                  TEXT("dll_search_path_override"), TEXT(""),
+                  &config.mono_dll_search_path_override);
     load_bool_file(config_path, TEXT("UnityMono"), TEXT("debug_enabled"),
                    TEXT("false"), &config.mono_debug_enabled);
     load_bool_file(config_path, TEXT("UnityMono"), TEXT("debug_suspend"),