diff --git a/R/app-driver-upload-file.R b/R/app-driver-upload-file.R
index 67c1772e..10f89f5d 100644
--- a/R/app-driver-upload-file.R
+++ b/R/app-driver-upload-file.R
@@ -21,9 +21,9 @@ app_upload_file <- function(
     "shinytest2.outputValuesWaiter.start(", toJSON_atomic(timeout_), ", 2);"
   ))
 
-
   filename <- inputs[[1]]
-  self$log_message(paste0("Uploading file for id: ", filename))
+  self$log_message(paste0("Uploading file(s) for id: ",
+                          paste(filename, collapse = ", ")))
 
   node_id <- app_find_node_id(self, private, input = names(inputs)[1])
 
@@ -42,7 +42,7 @@ app_upload_file <- function(
   )
 
   self$get_chromote_session()$DOM$setFileInputFiles(
-    files = list(fs::path_real(filename)),
+    files = as.list(fs::path_real(filename)),
     nodeId = node_id
   )
 
diff --git a/tests/testthat/apps/upload-multi/app.R b/tests/testthat/apps/upload-multi/app.R
new file mode 100644
index 00000000..9d47bdb1
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/app.R
@@ -0,0 +1,21 @@
+library(shiny)
+
+ui <- fluidPage(
+  "Upload multiple files:",
+  fileInput("files", label = NULL, multiple = TRUE),
+  verbatimTextOutput("file_out"),
+)
+
+server <- function(input, output) {
+
+  # Display `file` output
+  output$file_out <- renderPrint({
+    if (is.null(input$files))
+      return(NULL)
+    df <- input$files
+    df$datapath <- paste0("<tempdir>/", basename(df$datapath))
+    df
+  })
+}
+
+shinyApp(ui, server)
diff --git a/tests/testthat/apps/upload-multi/tests/testthat.R b/tests/testthat/apps/upload-multi/tests/testthat.R
new file mode 100644
index 00000000..7d25b5b9
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/tests/testthat.R
@@ -0,0 +1 @@
+shinytest2::test_app()
diff --git a/tests/testthat/apps/upload-multi/tests/testthat/_snaps/app-upload-multi/upload-multi-001.json b/tests/testthat/apps/upload-multi/tests/testthat/_snaps/app-upload-multi/upload-multi-001.json
new file mode 100644
index 00000000..34dac574
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/tests/testthat/_snaps/app-upload-multi/upload-multi-001.json
@@ -0,0 +1,28 @@
+{
+  "input": {
+    "files": {
+      "name": [
+        "cars.csv",
+        "cars_2.csv"
+      ],
+      "size": [
+        308,
+        229
+      ],
+      "type": [
+        "text/csv",
+        "text/csv"
+      ],
+      "datapath": [
+        "0.csv",
+        "1.csv"
+      ]
+    }
+  },
+  "output": {
+    "file_out": "        name size     type        datapath\n1   cars.csv  308 text/csv <tempdir>/0.csv\n2 cars_2.csv  229 text/csv <tempdir>/1.csv"
+  },
+  "export": {
+
+  }
+}
diff --git a/tests/testthat/apps/upload-multi/tests/testthat/_snaps/app-upload-multi/upload-multi-001_.png b/tests/testthat/apps/upload-multi/tests/testthat/_snaps/app-upload-multi/upload-multi-001_.png
new file mode 100644
index 00000000..34c5a719
Binary files /dev/null and b/tests/testthat/apps/upload-multi/tests/testthat/_snaps/app-upload-multi/upload-multi-001_.png differ
diff --git a/tests/testthat/apps/upload-multi/tests/testthat/cars.csv b/tests/testthat/apps/upload-multi/tests/testthat/cars.csv
new file mode 100644
index 00000000..5d0acdb9
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/tests/testthat/cars.csv
@@ -0,0 +1,51 @@
+"speed","dist"
+4,2
+4,10
+7,4
+7,22
+8,16
+9,10
+10,18
+10,26
+10,34
+11,17
+11,28
+12,14
+12,20
+12,24
+12,28
+13,26
+13,34
+13,34
+13,46
+14,26
+14,36
+14,60
+14,80
+15,20
+15,26
+15,54
+16,32
+16,40
+17,32
+17,40
+17,50
+18,42
+18,56
+18,76
+18,84
+19,36
+19,46
+19,68
+20,32
+20,48
+20,52
+20,56
+20,64
+22,66
+23,54
+24,70
+24,92
+24,93
+24,120
+25,85
diff --git a/tests/testthat/apps/upload-multi/tests/testthat/cars_2.csv b/tests/testthat/apps/upload-multi/tests/testthat/cars_2.csv
new file mode 100644
index 00000000..387076db
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/tests/testthat/cars_2.csv
@@ -0,0 +1,38 @@
+"speed","dist"
+4,2
+4,10
+7,4
+7,22
+8,16
+9,10
+10,18
+10,26
+10,34
+11,17
+11,28
+12,14
+12,20
+12,24
+12,28
+13,26
+13,34
+13,34
+13,46
+14,26
+14,36
+14,60
+14,80
+15,20
+15,26
+15,54
+16,32
+16,40
+17,32
+17,40
+17,50
+18,42
+18,56
+18,76
+18,84
+19,36
+19,46
diff --git a/tests/testthat/apps/upload-multi/tests/testthat/setup.R b/tests/testthat/apps/upload-multi/tests/testthat/setup.R
new file mode 100644
index 00000000..80d55d27
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/tests/testthat/setup.R
@@ -0,0 +1 @@
+shinytest2::load_app_env()
diff --git a/tests/testthat/apps/upload-multi/tests/testthat/test-app-upload-multi.R b/tests/testthat/apps/upload-multi/tests/testthat/test-app-upload-multi.R
new file mode 100644
index 00000000..baf64c2a
--- /dev/null
+++ b/tests/testthat/apps/upload-multi/tests/testthat/test-app-upload-multi.R
@@ -0,0 +1,13 @@
+library(shinytest2)
+
+test_that("Make sure upload can use two local files", {
+  app <- AppDriver$new(name = "upload-multi")
+
+  app$upload_file(files = c("cars.csv", "cars_2.csv"))
+  app$expect_values()
+
+  expect_error(
+    app$upload_file(files = "missing_file.csv"),
+    "Error finding upload file at path", fixed = TRUE
+  )
+})