diff --git a/MusicToSoundpad.vcxproj b/MusicToSoundpad.vcxproj
index 7c38f32..52233de 100644
--- a/MusicToSoundpad.vcxproj
+++ b/MusicToSoundpad.vcxproj
@@ -20,6 +20,10 @@
   </ItemGroup>
   <ItemGroup>
     <ClCompile Include="src\main.c" />
+    <ClCompile Include="src\md5.c" />
+  </ItemGroup>
+  <ItemGroup>
+    <ClInclude Include="src\md5.h" />
   </ItemGroup>
   <PropertyGroup Label="Globals">
     <VCProjectVersion>17.0</VCProjectVersion>
diff --git a/MusicToSoundpad.vcxproj.filters b/MusicToSoundpad.vcxproj.filters
index 0b7f47e..672ec92 100644
--- a/MusicToSoundpad.vcxproj.filters
+++ b/MusicToSoundpad.vcxproj.filters
@@ -18,5 +18,13 @@
     <ClCompile Include="src\main.c">
       <Filter>Source Files</Filter>
     </ClCompile>
+    <ClCompile Include="src\md5.c">
+      <Filter>Source Files</Filter>
+    </ClCompile>
+  </ItemGroup>
+  <ItemGroup>
+    <ClInclude Include="src\md5.h">
+      <Filter>Source Files</Filter>
+    </ClInclude>
   </ItemGroup>
 </Project>
\ No newline at end of file
diff --git a/src/main.c b/src/main.c
index 1e402ae..6767adb 100644
--- a/src/main.c
+++ b/src/main.c
@@ -3,6 +3,7 @@
 #include <stdio.h>
 #include <wchar.h>
 #include <Urlmon.h>
+#include "md5.h"
 
 #pragma comment(lib, "urlmon.lib")
 
@@ -30,7 +31,6 @@ BOOL DownloadFile(const wchar_t* url, const wchar_t* filePath) {
     }
 }
 
-// TODO: Compare the sums of the existing and latest binary to check for updates
 BOOL CheckAndDownloadYTDLP(const wchar_t* utilsFolderPath) {
     const wchar_t* ytDlpFileName = L"yt-dlp.exe";
     const wchar_t* ytDlpUrl = L"https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp.exe";
@@ -44,7 +44,12 @@ BOOL CheckAndDownloadYTDLP(const wchar_t* utilsFolderPath) {
         wprintf(L"Downloading yt-dlp.exe...\n");
         return DownloadFile(ytDlpUrl, ytDlpFilePath);
     } else {
-        wprintf(L"yt-dlp.exe already exists in the utils folder.\n");
+        wprintf(L"yt-dlp.exe already exists in the utils folder. Checking for updates...\n");
+        if (UpdateYTDLP() == 2)
+        {
+            wprintf(L"Updating yt-dlp.exe...\n");
+            return DownloadFile(ytDlpUrl, ytDlpFilePath);
+        }
         return TRUE;
     }
 }
diff --git a/src/md5.c b/src/md5.c
new file mode 100644
index 0000000..bc89185
--- /dev/null
+++ b/src/md5.c
@@ -0,0 +1,147 @@
+#include <stdio.h>
+#include <stdbool.h>
+#include <windows.h>
+#include <wininet.h>
+#include <wincrypt.h>
+
+#pragma comment(lib, "wininet.lib")
+#pragma comment(lib, "crypt32.lib")
+
+#define BUFSIZE 1024
+#define MD5_HASH_SIZE 16
+
+bool _DownloadFile(const char* url, const char* localFilePath) {
+    HINTERNET hInternet = InternetOpenA("MD5Check", INTERNET_OPEN_TYPE_DIRECT, NULL, NULL, 0);
+    if (hInternet == NULL) {
+        fprintf(stderr, "Error opening internet connection.\n");
+        return false;
+    }
+
+    HINTERNET hURL = InternetOpenUrlA(hInternet, url, NULL, 0, INTERNET_FLAG_RELOAD, 0);
+    if (hURL == NULL) {
+        fprintf(stderr, "Error opening URL: %s\n", url);
+        InternetCloseHandle(hInternet);
+        return false;
+    }
+
+    FILE* outputFile;
+    if (fopen_s(&outputFile, localFilePath, "wb") != 0 || outputFile == NULL) {
+        fprintf(stderr, "Error creating local file: %s\n", localFilePath);
+        InternetCloseHandle(hURL);
+        InternetCloseHandle(hInternet);
+        return false;
+    }
+
+    BYTE buffer[BUFSIZE];
+    DWORD bytesRead;
+    while (InternetReadFile(hURL, buffer, sizeof(buffer), &bytesRead) && bytesRead > 0) {
+        fwrite(buffer, 1, bytesRead, outputFile);
+    }
+
+    fclose(outputFile);
+    InternetCloseHandle(hURL);
+    InternetCloseHandle(hInternet);
+
+    return true;
+}
+
+bool CalculateMD5HashOfFile(const char* filename, BYTE* md5hash) {
+    HCRYPTPROV hProv = 0;
+    HCRYPTHASH hHash = 0;
+    HANDLE hFile = NULL;
+    BYTE rgbFile[BUFSIZE];
+    DWORD cbRead = 0;
+
+    if (!CryptAcquireContextA(&hProv, NULL, NULL, PROV_RSA_FULL, CRYPT_VERIFYCONTEXT)) {
+        return false;
+    }
+
+    if (!CryptCreateHash(hProv, CALG_MD5, 0, 0, &hHash)) {
+        CryptReleaseContext(hProv, 0);
+        return false;
+    }
+
+    hFile = CreateFileA(filename, GENERIC_READ, FILE_SHARE_READ, NULL, OPEN_EXISTING, FILE_FLAG_SEQUENTIAL_SCAN, NULL);
+    if (hFile == INVALID_HANDLE_VALUE) {
+        CryptDestroyHash(hHash);
+        CryptReleaseContext(hProv, 0);
+        return false;
+    }
+
+    while (ReadFile(hFile, rgbFile, BUFSIZE, &cbRead, NULL) && cbRead > 0) {
+        if (!CryptHashData(hHash, rgbFile, cbRead, 0)) {
+            CloseHandle(hFile);
+            CryptDestroyHash(hHash);
+            CryptReleaseContext(hProv, 0);
+            return false;
+        }
+    }
+
+    DWORD cbHash = MD5_HASH_SIZE;
+    if (!CryptGetHashParam(hHash, HP_HASHVAL, md5hash, &cbHash, 0)) {
+        CloseHandle(hFile);
+        CryptDestroyHash(hHash);
+        CryptReleaseContext(hProv, 0);
+        return false;
+    }
+
+    CloseHandle(hFile);
+    CryptDestroyHash(hHash);
+    CryptReleaseContext(hProv, 0);
+    return true;
+}
+
+int UpdateYTDLP() {
+    char* localFile = "utils\\yt-dlp.exe";
+    char* remoteURL = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp.exe";
+    BYTE localMD5[MD5_HASH_SIZE];
+    BYTE remoteMD5[MD5_HASH_SIZE];
+
+    char tempFilePath[MAX_PATH];
+    if (GetTempPathA(sizeof(tempFilePath), tempFilePath) == 0) {
+        fprintf(stderr, "Error getting temporary file path.\n");
+        return 1;
+    }
+
+    strcat_s(tempFilePath, sizeof(tempFilePath), "tempfile.dat");
+
+    if (!_DownloadFile(remoteURL, tempFilePath)) {
+        fprintf(stderr, "Error downloading remote file.\n");
+        return 1;
+    }
+
+    if (!CalculateMD5HashOfFile(localFile, localMD5)) {
+        fprintf(stderr, "Error calculating MD5 hash of local file.\n");
+        return 1;
+    }
+
+    if (!CalculateMD5HashOfFile(tempFilePath, remoteMD5)) {
+        fprintf(stderr, "Error calculating MD5 hash of remote file.\n");
+        return 1;
+    }
+
+    printf("Local MD5: ");
+    for (int i = 0; i < MD5_HASH_SIZE; i++) {
+        printf("%02x", localMD5[i]);
+    }
+    printf("\n");
+
+    printf("Remote MD5: ");
+    for (int i = 0; i < MD5_HASH_SIZE; i++) {
+        printf("%02x", remoteMD5[i]);
+    }
+    printf("\n");
+
+    if (memcmp(localMD5, remoteMD5, sizeof(localMD5)) == 0) {
+        printf("MD5 checksums match.\n");
+    } else {
+        printf("MD5 checksums do not match.\n");
+        return 2;
+    }
+
+    if (remove(tempFilePath) != 0) {
+        fprintf(stderr, "Error deleting temporary file.\n");
+    }
+
+    return 0;
+}
diff --git a/src/md5.h b/src/md5.h
new file mode 100644
index 0000000..931d3f8
--- /dev/null
+++ b/src/md5.h
@@ -0,0 +1,2 @@
+#pragma once
+int UpdateYTDLP();