diff --git a/Source/Core/Core/IOS/Network/Socket.cpp b/Source/Core/Core/IOS/Network/Socket.cpp
index ec0ae1641c..29af6231d0 100644
--- a/Source/Core/Core/IOS/Network/Socket.cpp
+++ b/Source/Core/Core/IOS/Network/Socket.cpp
@@ -19,6 +19,8 @@
 #include "Common/BitUtils.h"
 #include "Common/FileUtil.h"
 #include "Common/IOFile.h"
+#include "Common/Network.h"
+#include "Common/ScopeGuard.h"
 #include "Core/Config/MainSettings.h"
 #include "Core/Core.h"
 #include "Core/IOS/Device.h"
@@ -225,6 +227,7 @@ s32 WiiSocket::CloseFd()
     GetIOS()->EnqueueIPCReply(it->request, -SO_ENOTCONN);
     it = pending_sockops.erase(it);
   }
+  connecting_state = ConnectingState::None;
   return ReturnValue;
 }
 
@@ -297,6 +300,7 @@ void WiiSocket::Update(bool read, bool write, bool except)
 
         int ret = connect(fd, (sockaddr*)&local_name, sizeof(local_name));
         ReturnValue = WiiSockMan::GetNetErrorCode(ret, "SO_CONNECT", false);
+        UpdateConnectingState(ReturnValue);
 
         INFO_LOG_FMT(IOS_NET, "IOCTL_SO_CONNECT ({:08x}, {}:{}) = {}", wii_fd,
                      inet_ntoa(local_name.sin_addr), Common::swap16(local_name.sin_port), ret);
@@ -342,10 +346,12 @@ void WiiSocket::Update(bool read, bool write, bool except)
           {
             ReturnValue = -SO_ENETUNREACH;
             ResetTimeout();
+            connecting_state = ConnectingState::Error;
           }
           break;
         case -SO_EISCONN:
           ReturnValue = SO_SUCCESS;
+          connecting_state = ConnectingState::Connected;
           [[fallthrough]];
         default:
           ResetTimeout();
@@ -393,6 +399,24 @@ void WiiSocket::Update(bool read, bool write, bool except)
           {
           case IOCTLV_NET_SSL_DOHANDSHAKE:
           {
+            // The Wii allows a socket with an in-progress connection to
+            // perform the SSL handshake. MbedTLS doesn't support it so
+            // we have to check it manually.
+            connecting_state = GetConnectingState();
+            if (connecting_state == ConnectingState::Connecting)
+            {
+              WriteReturnValue(SSL_ERR_RAGAIN, BufferIn);
+              ReturnValue = SSL_ERR_RAGAIN;
+              break;
+            }
+            else if (connecting_state == ConnectingState::None ||
+                     connecting_state == ConnectingState::Error)
+            {
+              WriteReturnValue(SSL_ERR_SYSCALL, BufferIn);
+              ReturnValue = SSL_ERR_SYSCALL;
+              break;
+            }
+
             mbedtls_ssl_context* ctx = &NetSSLDevice::_SSL[sslID].ctx;
             const int ret = mbedtls_ssl_handshake(ctx);
             if (ret != 0)
@@ -673,6 +697,100 @@ void WiiSocket::Update(bool read, bool write, bool except)
   }
 }
 
+void WiiSocket::UpdateConnectingState(s32 connect_rv)
+{
+  if (connect_rv == -SO_EAGAIN || connect_rv == -SO_EALREADY || connect_rv == -SO_EINPROGRESS)
+  {
+    connecting_state = ConnectingState::Connecting;
+  }
+  else if (connect_rv >= 0)
+  {
+    connecting_state = ConnectingState::Connected;
+  }
+  else
+  {
+    connecting_state = ConnectingState::Error;
+  }
+}
+
+WiiSocket::ConnectingState WiiSocket::GetConnectingState() const
+{
+  const auto state = Common::SaveNetworkErrorState();
+  Common::ScopeGuard guard([&state] { Common::RestoreNetworkErrorState(state); });
+
+#ifdef _WIN32
+  constexpr int (*get_errno)() = &WSAGetLastError;
+#else
+  constexpr int (*get_errno)() = []() { return errno; };
+#endif
+
+  switch (connecting_state)
+  {
+  case ConnectingState::Error:
+  case ConnectingState::Connected:
+  case ConnectingState::None:
+    break;
+  case ConnectingState::Connecting:
+  {
+    const s32 nfds = fd + 1;
+    fd_set read_fds;
+    fd_set write_fds;
+    fd_set except_fds;
+    struct timeval t = {0, 0};
+    FD_ZERO(&read_fds);
+    FD_ZERO(&write_fds);
+    FD_ZERO(&except_fds);
+    FD_SET(fd, &write_fds);
+    FD_SET(fd, &except_fds);
+
+    auto& sm = WiiSockMan::GetInstance();
+    if (select(nfds, &read_fds, &write_fds, &except_fds, &t) < 0)
+    {
+      const s32 error = get_errno();
+      ERROR_LOG_FMT(IOS_SSL, "Failed to get socket (fd={}) connection state (err={}): {}", wii_fd,
+                    error, sm.DecodeError(error));
+      return ConnectingState::Error;
+    }
+
+    if (FD_ISSET(fd, &write_fds) == 0 && FD_ISSET(fd, &except_fds) == 0)
+      break;
+
+    s32 error = 0;
+    socklen_t len = sizeof(error);
+    if (getsockopt(fd, SOL_SOCKET, SO_ERROR, reinterpret_cast<char*>(&error), &len) != 0)
+    {
+      error = get_errno();
+      ERROR_LOG_FMT(IOS_SSL, "Failed to get socket (fd={}) error state (err={}): {}", wii_fd, error,
+                    sm.DecodeError(error));
+      return ConnectingState::Error;
+    }
+
+    if (error != 0)
+    {
+      ERROR_LOG_FMT(IOS_SSL, "Non-blocking connect (fd={}) failed (err={}): {}", wii_fd, error,
+                    sm.DecodeError(error));
+      return ConnectingState::Error;
+    }
+
+    // Get peername to ensure the socket is connected
+    sockaddr_in peer;
+    socklen_t peer_len = sizeof(peer);
+    if (getpeername(fd, reinterpret_cast<sockaddr*>(&peer), &peer_len) != 0)
+    {
+      error = get_errno();
+      ERROR_LOG_FMT(IOS_SSL, "Non-blocking connect (fd={}) failed to get peername (err={}): {}",
+                    wii_fd, error, sm.DecodeError(error));
+      return ConnectingState::Error;
+    }
+
+    INFO_LOG_FMT(IOS_SSL, "Non-blocking connect (fd={}) succeeded", wii_fd);
+    return ConnectingState::Connected;
+  }
+  }
+
+  return connecting_state;
+}
+
 const WiiSocket::Timeout& WiiSocket::GetTimeout()
 {
   if (!timeout.has_value())
diff --git a/Source/Core/Core/IOS/Network/Socket.h b/Source/Core/Core/IOS/Network/Socket.h
index 8f6e02a8bb..9e2509fcc0 100644
--- a/Source/Core/Core/IOS/Network/Socket.h
+++ b/Source/Core/Core/IOS/Network/Socket.h
@@ -199,6 +199,14 @@ private:
     void Abort(s32 value);
   };
 
+  enum class ConnectingState
+  {
+    None,
+    Connecting,
+    Connected,
+    Error
+  };
+
   friend class WiiSockMan;
   void SetFd(s32 s);
   void SetWiiFd(s32 s);
@@ -212,11 +220,14 @@ private:
   void DoSock(Request request, NET_IOCTL type);
   void DoSock(Request request, SSL_IOCTL type);
   void Update(bool read, bool write, bool except);
+  void UpdateConnectingState(s32 connect_rv);
+  ConnectingState GetConnectingState() const;
   bool IsValid() const { return fd >= 0; }
 
   s32 fd = -1;
   s32 wii_fd = -1;
   bool nonBlock = false;
+  ConnectingState connecting_state = ConnectingState::None;
   std::list<sockop> pending_sockops;
 
   std::optional<Timeout> timeout;