I've followed this blogpost: https://medium.com/@PaulinaSadowska/display-progress-of-multipart-request-with-retrofit-and-rxjava-23a4a779e6ba and then made the following adjustments to display the total progression instead of progression of separate files:
  private fun prepareFileParts(reportAttachments: MutableList<ReportAttachment>, emitter: FlowableEmitter<Double>): List<MultipartBody.Part> {
    val multiPartBodyList = mutableListOf<MultipartBody.Part>()
    var offset = 0L
    var totalLength = 0L
    // calculate the total length of all files
    for (attachment in reportAttachments) {
        val file = File(attachment.filePath)
        totalLength += file.length()
    }
    // create requestbody for each file and calculate the progression offset
    for (attachment in reportAttachments) {
        val file = File(attachment.filePath)
        val mimeType = attachment.mimeType
        val countingRequestBody = createCountingRequestBody(file, mimeType, emitter, offset, totalLength)
        offset += file.length()
        val multipartBody = MultipartBody.Part.createFormData("file", file.name, countingRequestBody)
        multiPartBodyList.add(multipartBody)
    }
    return multiPartBodyList
}
private fun createCountingRequestBody(file: File, mimeType: String, emitter: FlowableEmitter<Double>, offset: Long, totalLength: Long): RequestBody {
    val requestBody = RequestBody.create(MediaType.parse(mimeType), file)
    return CountingRequestBody(requestBody, object : CountingRequestBody.Listener {
        override fun onRequestProgress(bytesWritten: Long, contentLength: Long) {
            val progress: Double = 1.0 * (offset + bytesWritten) / totalLength
            emitter.onNext(progress)
        }
    })
}
If you want, you can also create an interceptor and add it to your OkHttpClient. This would track all outgoing API calls by default. It would look something like this: 
class UploadProgressInterceptor(private val progressListener: CountingRequestBody.Listener) : Interceptor {
override fun intercept(chain: Interceptor.Chain): Response {
    val originalRequest = chain.request()
    if (originalRequest.body() == null) {
        return chain.proceed(originalRequest)
    }
    val requestBody = originalRequest.body()
    requestBody?.let {
        val progressRequest = originalRequest.newBuilder()
                .method(originalRequest.method(), CountingRequestBody(it, progressListener))
                .build()
        return chain.proceed(progressRequest)
    }
    return chain.proceed(originalRequest)
}