diff --git a/src/client/cli/cmd/transfer.cpp b/src/client/cli/cmd/transfer.cpp
index 85e57ecb95..53e09aaa08 100644
--- a/src/client/cli/cmd/transfer.cpp
+++ b/src/client/cli/cmd/transfer.cpp
@@ -25,6 +25,8 @@
 
 #include <fmt/std.h>
 
+#include <QRegularExpression>
+
 namespace mp = multipass;
 namespace cmd = multipass::cmd;
 namespace mcp = multipass::cli::platform;
@@ -163,9 +165,16 @@ std::vector<std::pair<std::string, fs::path>> cmd::Transfer::args_to_instance_an
     instance_entry_args.reserve(args.size());
     for (const auto& entry : args)
     {
+        // this is needed so that Windows absolute paths are not split at the colon following the drive letter
+        if (QRegularExpression{R"(^[A-Za-z]:\\.*)"}.match(entry).hasMatch())
+        {
+            instance_entry_args.emplace_back("", entry.toStdString());
+            continue;
+        }
+
         const auto source_components = entry.split(':');
         const auto instance_name = source_components.size() == 1 ? "" : source_components.first().toStdString();
-        const auto file_path = source_components.size() == 1 ? source_components.first() : source_components.at(1);
+        const auto file_path = source_components.size() == 1 ? source_components.first() : entry.section(':', 1);
         if (!instance_name.empty())
             request.add_instance_name()->append(instance_name);
         instance_entry_args.emplace_back(instance_name, file_path.isEmpty() ? "." : file_path.toStdString());
diff --git a/tests/test_cli_client.cpp b/tests/test_cli_client.cpp
index a6f902ba9d..6cc601ff24 100644
--- a/tests/test_cli_client.cpp
+++ b/tests/test_cli_client.cpp
@@ -603,7 +603,8 @@ TEST_F(Client, transfer_cmd_local_source_instance_target)
     auto mocked_sftp_client_p = mocked_sftp_client.get();
 
     EXPECT_CALL(*mocked_sftp_utils, make_SFTPClient).WillOnce(Return(std::move(mocked_sftp_client)));
-    EXPECT_CALL(*mocked_sftp_client_p, push).WillOnce(Return(true));
+    EXPECT_CALL(*mocked_sftp_client_p, push).WillRepeatedly(Return(true));
+    EXPECT_CALL(*mocked_sftp_client_p, is_remote_dir).WillOnce(Return(true));
     EXPECT_CALL(mock_daemon, ssh_info)
         .WillOnce([](auto, grpc::ServerReaderWriter<mp::SSHInfoReply, mp::SSHInfoRequest>* server) {
             mp::SSHInfoReply reply;
@@ -612,7 +613,7 @@ TEST_F(Client, transfer_cmd_local_source_instance_target)
             return grpc::Status{};
         });
 
-    EXPECT_EQ(send_command({"transfer", "foo", "test-vm:bar"}), mp::ReturnCode::Ok);
+    EXPECT_EQ(send_command({"transfer", "foo", "C:\\Users\\file", "test-vm:bar"}), mp::ReturnCode::Ok);
 }
 
 TEST_F(Client, transfer_cmd_help_ok)