diff --git a/client.go b/client.go
index bf41ffb9..d274b007 100644
--- a/client.go
+++ b/client.go
@@ -418,8 +418,18 @@ var requestID int32
 var logSensitiveContent = os.Getenv("MAUTRIX_LOG_SENSITIVE_CONTENT") == "yes"
 
 func (params *FullRequest) compileRequest(ctx context.Context) (*http.Request, error) {
+	reqID := atomic.AddInt32(&requestID, 1)
+	logger := zerolog.Ctx(ctx)
+	if logger.GetLevel() == zerolog.Disabled || logger == zerolog.DefaultContextLogger {
+		logger = params.Logger
+	}
+	ctx = logger.With().
+		Int32("req_id", reqID).
+		Logger().WithContext(ctx)
+
 	var logBody any
-	reqBody := params.RequestBody
+	var reqBody io.Reader
+	var reqLen int64
 	if params.RequestJSON != nil {
 		jsonStr, err := json.Marshal(params.RequestJSON)
 		if err != nil {
@@ -434,12 +444,22 @@ func (params *FullRequest) compileRequest(ctx context.Context) (*http.Request, e
 			logBody = params.RequestJSON
 		}
 		reqBody = bytes.NewReader(jsonStr)
+		reqLen = int64(len(jsonStr))
 	} else if params.RequestBytes != nil {
 		logBody = fmt.Sprintf("<%d bytes>", len(params.RequestBytes))
 		reqBody = bytes.NewReader(params.RequestBytes)
-		params.RequestLength = int64(len(params.RequestBytes))
-	} else if params.RequestLength > 0 && params.RequestBody != nil {
-		logBody = fmt.Sprintf("<%d bytes>", params.RequestLength)
+		reqLen = int64(len(params.RequestBytes))
+	} else if params.RequestBody != nil {
+		logBody = "<unknown stream of bytes>"
+		reqLen = -1
+		if params.RequestLength > 0 {
+			logBody = fmt.Sprintf("<%d bytes>", params.RequestLength)
+			reqLen = params.RequestLength
+		} else if params.RequestLength == 0 {
+			zerolog.Ctx(ctx).Warn().
+				Msg("RequestBody passed without specifying request length")
+		}
+		reqBody = params.RequestBody
 		if rsc, ok := params.RequestBody.(io.ReadSeekCloser); ok {
 			// Prevent HTTP from closing the request body, it might be needed for retries
 			reqBody = nopCloseSeeker{rsc}
@@ -448,15 +468,8 @@ func (params *FullRequest) compileRequest(ctx context.Context) (*http.Request, e
 		params.RequestJSON = struct{}{}
 		logBody = params.RequestJSON
 		reqBody = bytes.NewReader([]byte("{}"))
+		reqLen = 2
 	}
-	reqID := atomic.AddInt32(&requestID, 1)
-	logger := zerolog.Ctx(ctx)
-	if logger.GetLevel() == zerolog.Disabled || logger == zerolog.DefaultContextLogger {
-		logger = params.Logger
-	}
-	ctx = logger.With().
-		Int32("req_id", reqID).
-		Logger().WithContext(ctx)
 	ctx = context.WithValue(ctx, LogBodyContextKey, logBody)
 	ctx = context.WithValue(ctx, LogRequestIDContextKey, int(reqID))
 	req, err := http.NewRequestWithContext(ctx, params.Method, params.URL, reqBody)
@@ -472,9 +485,7 @@ func (params *FullRequest) compileRequest(ctx context.Context) (*http.Request, e
 	if params.RequestJSON != nil {
 		req.Header.Set("Content-Type", "application/json")
 	}
-	if params.RequestLength > 0 && params.RequestBody != nil {
-		req.ContentLength = params.RequestLength
-	}
+	req.ContentLength = reqLen
 	return req, nil
 }