diff --git a/common/common.cpp b/common/common.cpp
index e890ca3993..fa533646e2 100644
--- a/common/common.cpp
+++ b/common/common.cpp
@@ -692,6 +692,49 @@ bool string_parse_kv_override(const char * data, std::vector<llama_model_kv_over
 // Filesystem utils
 //
 
+// Normalizes a relative filepath
+// - Replaces backslashes and forward slashes with the system path separator
+// - Trims leading './' or '.\' segments
+// - Trims leading '/' or '\' (treat 'root' as relative)
+// - Trims duplicate directory separators
+// - Does not resolve '..' segments
+// - Does not ensure the path is valid or safe
+// Use in conjunction with `fs_validate_filename`, calling `fs_validate_filename` after `fs_normalize_filepath`
+std::string fs_normalize_filepath(const std::string & path) {
+    std::string result;
+    result.reserve(path.size());
+
+    bool leading = true;
+    char prev = 0;
+    for (size_t i = 0; i < path.size(); ++i) {
+        char c = path[i];
+        if (c == '/' || c == '\\') {
+            c = DIRECTORY_SEPARATOR;
+        }
+        if (leading) {
+            if (c == DIRECTORY_SEPARATOR) {
+                continue; // Skip leading separators
+            } else if (c == '.') {
+                if (i + 1 < path.size()) {
+                    char next = path[i + 1];
+                    if (next == '/' || next == '\\') {
+                        ++i;
+                        continue; // Skip leading dot segments
+                    }
+                }
+            }
+            leading = false;
+        }
+        if (prev == DIRECTORY_SEPARATOR && c == DIRECTORY_SEPARATOR) {
+            continue; // Skip duplicate separators
+        }
+        prev = c;
+        result += c;
+    }
+
+    return result;
+}
+
 // Validate if a filename or path is safe to use
 bool fs_validate_filename(const std::string & filename, bool allow_subdirs) {
     if (!filename.length()) {
diff --git a/common/common.h b/common/common.h
index b284244530..746f40cc55 100644
--- a/common/common.h
+++ b/common/common.h
@@ -707,6 +707,7 @@ std::string string_from(const struct llama_context * ctx, const struct llama_bat
 // Filesystem utils
 //
 
+std::string fs_normalize_filepath(const std::string & path);
 bool fs_validate_filename(const std::string & filename, bool allow_subdirs = false);
 bool fs_create_directory_with_parents(const std::string & path);
 bool fs_is_directory(const std::string & path);
diff --git a/tests/test-fs-validate-filename.cpp b/tests/test-fs-validate-filename.cpp
index 24cdfc6ac6..5a194fef1a 100644
--- a/tests/test-fs-validate-filename.cpp
+++ b/tests/test-fs-validate-filename.cpp
@@ -9,6 +9,17 @@
 static int n_tests  = 0;
 static int n_failed = 0;
 
+static const char SEP = DIRECTORY_SEPARATOR;
+
+static void test_normalize(const char * desc, const std::string & expected, const std::string & input) {
+    std::string result = fs_normalize_filepath(input);
+    n_tests++;
+    if (result != expected) {
+        n_failed++;
+        printf("  FAIL: %s (got \"%s\", expected \"%s\")\n", desc, result.c_str(), expected.c_str());
+    }
+}
+
 static void test(const char * desc, bool expected, const std::string & filename, bool allow_subdirs = false) {
     bool result = fs_validate_filename(filename, allow_subdirs);
     n_tests++;
@@ -40,6 +51,7 @@ int main(void) {
     test("leading space",           false, " foo");
     test("trailing space",          false, "foo ");
     test("trailing dot",            false, "foo.");
+    test("dot path",                false, "./././");
 
     // --- Double dots ---
     test("contains double dot",     true,  "foo..bar");
@@ -104,6 +116,7 @@ int main(void) {
     test("trailing slash",          true,  "foo/bar/",          true);
     test("colon in path",           false, "foo/b:r/baz",       true);
     test("control char in path",    false, "foo/b\nar/baz",     true);
+    test("dot path",                false, "./././",            true);
 
     // --- Leading separators ---
     test("leading slash",           false, "/foo/bar",          true);
@@ -125,6 +138,23 @@ int main(void) {
     test("trailing space before slash",     false, "bar /baz",         true);
     test("trailing dot before slash",       false, "bar./baz",         true);
 
+    // --- fs_normalize_filepath ---
+    test_normalize("passthrough simple",        "foo.txt",                              "foo.txt");
+    test_normalize("passthrough subdir",        std::string("foo") + SEP + "bar.txt",   "foo/bar.txt");
+    test_normalize("backslash to sep",          std::string("foo") + SEP + "bar.txt",   "foo\\bar.txt");
+    test_normalize("mixed separators",          std::string("a") + SEP + "b" + SEP + "c", "a/b\\c");
+    test_normalize("duplicate slashes",         std::string("foo") + SEP + "bar",       "foo//bar");
+    test_normalize("duplicate backslashes",     std::string("foo") + SEP + "bar",       "foo\\\\bar");
+    test_normalize("triple slashes",            std::string("foo") + SEP + "bar",       "foo///bar");
+    test_normalize("leading slash stripped",     "foo",                                  "/foo");
+    test_normalize("leading backslash stripped", "foo",                                  "\\foo");
+    test_normalize("multiple leading slashes",   "foo",                                 "///foo");
+    test_normalize("leading dot-slash stripped",  "foo",                                "./foo");
+    test_normalize("leading dot-backslash stripped", "foo",                             ".\\foo");
+    test_normalize("deep path normalized",
+        std::string("a") + SEP + "b" + SEP + "c" + SEP + "d.txt",
+        "/a//b\\c/d.txt");
+
     if (n_failed) {
         printf("\n%d/%d tests failed\n", n_failed, n_tests);
         fflush(stdout);
diff --git a/tools/server/server-common.cpp b/tools/server/server-common.cpp
index a853f65c8d..836275cacc 100644
--- a/tools/server/server-common.cpp
+++ b/tools/server/server-common.cpp
@@ -798,6 +798,7 @@ static void handle_media(
         }
         // load local image file
         std::string file_path = url.substr(7); // remove "file://"
+        file_path = fs_normalize_filepath(file_path); // remove any leading './' and normalize separators
         raw_buffer data;
         if (!fs_validate_filename(file_path, true)) {
             throw std::invalid_argument("file path is not allowed: " + file_path);