diff --git a/R/checks.R b/R/checks.R
index e763c864..b34102b1 100644
--- a/R/checks.R
+++ b/R/checks.R
@@ -712,3 +712,32 @@ check_fields_are_checkboxes <- function(metadata_tbl, call = caller_env()) {
     )
   }
 }
+
+#' @title
+#' Check values_to length against detected number of checkbox fields
+#'
+#' @param col_groups a list of column groups identified by checkbox field detection
+#' @param values_to a user defined character vector passed from [combine_checkboxes()]
+#' @param call The calling environment to use in the error message
+#'
+#' @keywords internal
+check_values_to_length <- function(col_groups, values_to, call = caller_env()) {
+  if (length(values_to) < length(names(col_groups))) {
+    cli_warn(
+      message = c(
+        `!` = "Detected fewer {.code values_to} arguments than the number of checkbox fields. Only the first {length(values_to)} will be used."
+      ),
+      class = c("checkbox_value_to_length", "REDCapTidieR_cond")
+    )
+  }
+
+  if (length(values_to) > length(names(col_groups))) {
+    cli_abort(
+      message = c(
+        `x` = "The number of {.code values_to} arguments supplied is greater than the number of checkbox fields detected.",
+        `i` = "{length(values_to)} {.code values_to} supplied, {length(names(col_groups))} checkbox fields detected."
+      ),
+      class = c("checkbox_value_to_length", "REDCapTidieR_cond")
+    )
+  }
+}
diff --git a/R/combine_checkboxes.R b/R/combine_checkboxes.R
index 4f61625c..50dba153 100644
--- a/R/combine_checkboxes.R
+++ b/R/combine_checkboxes.R
@@ -48,68 +48,81 @@ combine_checkboxes <- function(supertbl,
   # Check args ---
   check_arg_is_supertbl(supertbl, req_cols = c("redcap_data", "redcap_metadata"))
   check_arg_is_character(tbl, len = 1, any.missing = FALSE)
-  check_arg_is_character(values_to, len = 1, any.missing = FALSE)
+  check_arg_is_character(values_to, any.missing = FALSE)
   check_arg_is_character(multi_value_label, len = 1, any.missing = TRUE)
   check_arg_is_character(values_fill, len = 1, any.missing = TRUE)
   check_arg_choices(raw_or_label, choices = c("label", "raw"))
   check_arg_is_logical(keep, len = 1, any.missing = FALSE)
 
-  # Save user cols to enquosure
-  cols_exp <- enquo(cols)
-
   # Extract tbl from supertbl
   data_tbl <- supertbl %>%
     extract_tibble(tbl)
 
-  # Get field names from cols_exp, check that fields exist
-  field_names <- names(eval_select(cols_exp, data = data_tbl))
-  check_fields_exist(fields = field_names, expr = cols_exp)
+  # Save user cols to quosure
+  cols_exp <- enquo(cols)
 
-  # Define values_to as the count of TRUEs/1s for the given checkbox field
-  # Assign TRUE if multiple selections made, and FALSE if one or zero made
-  data_tbl_mod <- data_tbl %>%
-    mutate(
-      !!values_to := case_when(
-        rowSums(select(., eval_tidy(cols_exp))) > 1 ~ TRUE,
-        TRUE ~ FALSE
-      )
-    )
+  # Evaluate the cols expression to get the selected column names
+  selected_cols <- names(eval_select(cols_exp, data = data_tbl))
+  check_fields_exist(fields = selected_cols, expr = cols_exp) # Check supplied fields exist
+
+  # Extract the prefix of each selected column
+  prefixes <- sub("___.*", "", selected_cols)
+
+  # Split the selected columns based on their prefixes
+  col_groups <- split(selected_cols, prefixes)
+  check_values_to_length(col_groups, values_to) # Check values_to columns match length of fields
 
   # Get metadata reference table, check that chosen fields are checkboxes
   metadata_tbl <- supertbl$redcap_metadata[supertbl$redcap_form_name == tbl][[1]]
-  metadata_ref <- get_metadata_ref(metadata_tbl, field_names)
+  metadata_ref <- get_metadata_ref(metadata_tbl, selected_cols)
+
+  # Define values_to as the count of TRUEs/1s for the given checkbox field
+  # Assign TRUE if multiple selections made, and FALSE if one or zero made
+  data_tbl_mod <- data_tbl
+
+  for (i in seq_along(values_to)) {
+    data_tbl_mod <- data_tbl_mod %>%
+      mutate(
+        !!values_to[i] := case_when(
+          rowSums(select(., col_groups[[i]])) > 1 ~ TRUE,
+          .default = FALSE
+        )
+      )
+  }
 
   # Replace TRUEs/1s with raw/label values from metadata
   data_tbl_mod <- data_tbl_mod %>%
     mutate(across(
-      field_names,
+      selected_cols,
       ~ replace_true(.x,
-        cur_column(),
-        metadata = metadata_ref,
-        raw_or_label = raw_or_label
+                     cur_column(),
+                     metadata = metadata_ref,
+                     raw_or_label = raw_or_label
       )
-    ))
+    ),
+    across(selected_cols, as.character) # enforce to character strings
+    )
 
-  # Convert values_to from TRUE/FALSE to multi_value_label or identified single val
-  data_tbl_mod <- data_tbl_mod %>%
-    mutate(
-      across(field_names, as.character) # enforce to character strings
-    ) %>%
-    mutate(
-      !!values_to := ifelse(!!sym(values_to),
-        multi_value_label,
-        coalesce(!!!syms(field_names))
-      ),
-      !!values_to := ifelse(is.na(!!sym(values_to)),
-        values_fill,
-        !!sym(values_to)
+  for (i in seq_along(values_to)) {
+    metadata_overwrite <- metadata_ref %>% filter(field_name %in% col_groups[[i]]) %>% pull(raw_or_label)
+
+    data_tbl_mod <- data_tbl_mod %>%
+      mutate(
+        !!values_to[i] := ifelse(!!sym(values_to[i]),
+                                 multi_value_label,
+                                 coalesce(!!!syms(col_groups[[i]]))
+        ),
+        !!values_to[i] := ifelse(is.na(!!sym(values_to[i])),
+                                 values_fill,
+                                 !!sym(values_to[i])
+        )
+      ) %>%
+      mutate(
+        !!values_to[i] := factor(!!sym(values_to[i]),
+                                 levels = c(metadata_overwrite, multi_value_label, values_fill)
+        )
       )
-    ) %>%
-    mutate(
-      !!values_to := factor(!!sym(values_to),
-        levels = c(metadata_ref[[raw_or_label]], multi_value_label, values_fill)
-      )
-    )
+  }
 
   final_tbl <- bind_cols(
     data_tbl,
@@ -119,7 +132,7 @@ combine_checkboxes <- function(supertbl,
   # Keep or remove original multi columns
   if (!keep) {
     final_tbl <- final_tbl %>%
-      select(-field_names)
+      select(-selected_cols)
   }
 
   # Update the supertbl data tibble
@@ -131,17 +144,16 @@ combine_checkboxes <- function(supertbl,
 #' @title Utility function for getting metadata raw and label values for checkboxes
 #'
 #' @param metadata_tbl A metadata tibble from the supertibble generated by [read_redcap()].
-#' @param field_names Character string vector of field names for checkbox combination
+#' @param selected_cols Character string vector of field names for checkbox combination
 #'
 #' @returns a tibble
 #'
 #' @keywords internal
 get_metadata_ref <- function(metadata_tbl,
-                             field_names) {
+                             selected_cols) {
   # Create a metadata reference table linking field name to raw and label values
   out <- metadata_tbl %>%
-    filter(.data$field_name %in% field_names) %>%
-    # TODO: original_field a temporary placeholder for future multi-field and mapping dev
+    filter(.data$field_name %in% selected_cols) %>%
     mutate(
       original_field = sub("___.*$", "", .data$field_name)
     )
@@ -149,11 +161,19 @@ get_metadata_ref <- function(metadata_tbl,
   # Make sure selection is checkbox metadata field type
   check_fields_are_checkboxes(out)
 
-  # TODO: Make more robust for multi-field and mapping, using original_field above
-  parsed_vals <- parse_labels(first(out$select_choices_or_calculations))
+  # Bind raw/label values per original field grouping
+  parsed_vals <- tibble()
+
+  for (i in seq_along(unique(out$original_field))) {
+    index <- unique(out$original_field)[i]
+    out_filtered <- out %>% filter(original_field == index)
+
+    parsed_vals <- rbind(parsed_vals, parse_labels(first(out_filtered$select_choices_or_calculations)))
+  }
 
   bind_cols(out, parsed_vals) %>%
-    select(.data$field_name, .data$raw, .data$label)
+    select(.data$field_name, .data$raw, .data$label, original_field) %>%
+    relocate(original_field, .after = field_name)
 }
 
 #' @noRd
diff --git a/man/check_values_to_length.Rd b/man/check_values_to_length.Rd
new file mode 100644
index 00000000..e9194a08
--- /dev/null
+++ b/man/check_values_to_length.Rd
@@ -0,0 +1,19 @@
+% Generated by roxygen2: do not edit by hand
+% Please edit documentation in R/checks.R
+\name{check_values_to_length}
+\alias{check_values_to_length}
+\title{Check values_to length against detected number of checkbox fields}
+\usage{
+check_values_to_length(col_groups, values_to, call = caller_env())
+}
+\arguments{
+\item{col_groups}{a list of column groups identified by checkbox field detection}
+
+\item{values_to}{a user defined character vector passed from \code{\link[=combine_checkboxes]{combine_checkboxes()}}}
+
+\item{call}{The calling environment to use in the error message}
+}
+\description{
+Check values_to length against detected number of checkbox fields
+}
+\keyword{internal}
diff --git a/man/get_metadata_ref.Rd b/man/get_metadata_ref.Rd
index 2c09c4bb..6ced220b 100644
--- a/man/get_metadata_ref.Rd
+++ b/man/get_metadata_ref.Rd
@@ -4,12 +4,12 @@
 \alias{get_metadata_ref}
 \title{Utility function for getting metadata raw and label values for checkboxes}
 \usage{
-get_metadata_ref(metadata_tbl, field_names)
+get_metadata_ref(metadata_tbl, selected_cols)
 }
 \arguments{
 \item{metadata_tbl}{A metadata tibble from the supertibble generated by \code{\link[=read_redcap]{read_redcap()}}.}
 
-\item{field_names}{Character string vector of field names for checkbox combination}
+\item{selected_cols}{Character string vector of field names for checkbox combination}
 }
 \value{
 a tibble
diff --git a/tests/testthat/test-checks.R b/tests/testthat/test-checks.R
index 77435375..3fc71072 100644
--- a/tests/testthat/test-checks.R
+++ b/tests/testthat/test-checks.R
@@ -272,3 +272,22 @@ test_that("check_fields_are_checkboxes works", {
   expect_error(check_fields_are_checkboxes(metadata), class = "non_checkbox_fields")
   expect_no_error(check_fields_are_checkboxes(metadata_filtered))
 })
+
+test_that("check_values_to_length length works", {
+  col_groups <- list(
+    checkbox_1 = c("checkbox1___1", "checkbox1___2"),
+    checkbox_2 = c("checkbox2___1")
+  )
+
+  values_to <- c("new_col1", "new_col2")
+
+  expect_no_message(check_values_to_length(col_groups, values_to))
+
+  values_to_warn <- "new_col1"
+
+  expect_warning(check_values_to_length(col_groups, values_to_warn), class = "checkbox_value_to_length")
+
+  values_to_error <- c("new_col1", "new_col2", "new_col3")
+
+  expect_error(check_values_to_length(col_groups, values_to_error), class = "checkbox_value_to_length")
+})
diff --git a/tests/testthat/test-combine_checkboxes.R b/tests/testthat/test-combine_checkboxes.R
index 45abb426..bb7af8f2 100644
--- a/tests/testthat/test-combine_checkboxes.R
+++ b/tests/testthat/test-combine_checkboxes.R
@@ -1,8 +1,8 @@
 nonrepeat_data <- tibble::tribble(
-  ~"study_id", ~"multi___1", ~"multi___2", ~"multi___3", ~"extra_data",
-  1, TRUE, FALSE, FALSE, 1,
-  2, TRUE, TRUE, FALSE, 2,
-  3, FALSE, FALSE, FALSE, 3
+  ~"study_id", ~"multi___1", ~"multi___2", ~"multi___3", ~"single_checkbox___1", ~"extra_data",
+  1, TRUE, FALSE, FALSE, TRUE, 1,
+  2, TRUE, TRUE, FALSE, TRUE, 2,
+  3, FALSE, FALSE, FALSE, FALSE, 3
 )
 
 nonrepeat_metadata <- tibble::tribble(
@@ -11,7 +11,8 @@ nonrepeat_metadata <- tibble::tribble(
   "multi___1", "checkbox", "1, Red | 2, Yellow | 3, Blue",
   "multi___2", "checkbox", "1, Red | 2, Yellow | 3, Blue",
   "multi___3", "checkbox", "1, Red | 2, Yellow | 3, Blue",
-  "extra_data", "dropdown", "1, 1 | 2, 2 | 3,3"
+  "single_checkbox___1", "checkbox", "4, Green",
+  "extra_data", "dropdown", "1, 1 | 2, 2 | 3, 3"
 )
 
 repeat_data <- tibble::tribble(
@@ -62,10 +63,10 @@ test_that("combine_checkboxes works for nonrepeat instrument", {
     dplyr::first()
 
   expected_out <- tibble::tribble(
-    ~"study_id", ~"multi___1", ~"multi___2", ~"multi___3", ~"extra_data", ~"new_col",
-    1, TRUE, FALSE, FALSE, 1, "Red",
-    2, TRUE, TRUE, FALSE, 2, "multiple",
-    3, FALSE, FALSE, FALSE, 3, "none"
+    ~"study_id", ~"multi___1", ~"multi___2", ~"multi___3", ~"single_checkbox___1", ~"extra_data", ~"new_col",
+    1, TRUE, FALSE, FALSE, TRUE, 1, "Red",
+    2, TRUE, TRUE, FALSE, TRUE, 2, "multiple",
+    3, FALSE, FALSE, FALSE, FALSE, 3, "none"
   ) %>%
     mutate(
       new_col = factor(new_col, levels = c("Red", "Yellow", "Blue", "multiple", "none"))
@@ -86,10 +87,10 @@ test_that("combine_checkboxes works for nonrepeat instrument and drop old values
     dplyr::first()
 
   expected_out <- tibble::tribble(
-    ~"study_id", ~"extra_data", ~"new_col",
-    1, 1, "Red",
-    2, 2, "Multiple",
-    3, 3, NA
+    ~"study_id", ~"single_checkbox___1", ~"extra_data", ~"new_col",
+    1, TRUE, 1, "Red",
+    2, TRUE, 2, "Multiple",
+    3, FALSE, 3, NA
   ) %>%
     mutate(
       new_col = factor(new_col, levels = c("Red", "Yellow", "Blue", "Multiple"))
@@ -124,14 +125,14 @@ test_that("combine_checkboxes works for repeat instrument", {
 test_that("get_metadata_ref works", {
   out <- get_metadata_ref(
     metadata_tbl = supertbl$redcap_metadata[[1]],
-    field_names = c("multi___1", "multi___2", "multi___3")
+    selected_cols = c("multi___1", "multi___2", "multi___3")
   )
 
   expected_out <- tibble::tribble(
-    ~"field_name", ~"raw", ~"label",
-    "multi___1", "1", "Red",
-    "multi___2", "2", "Yellow",
-    "multi___3", "3", "Blue"
+    ~"field_name", ~"original_field", ~"raw", ~"label",
+    "multi___1", "multi", "1", "Red",
+    "multi___2", "multi", "2", "Yellow",
+    "multi___3", "multi", "3", "Blue"
   )
 
   expect_equal(out, expected_out)
@@ -155,3 +156,53 @@ test_that("replace_true works", {
 
   expect_equal(out, expected_out)
 })
+
+test_that("combine_checkboxes works for multiple checkbox fields", {
+  out <- combine_checkboxes(
+    supertbl = supertbl,
+    tbl = "nonrepeat_instrument",
+    cols = c(starts_with("multi"), starts_with("single_checkbox")),
+    values_to = c("new_col1", "new_col2"),
+    keep = FALSE
+  ) %>%
+    pull(redcap_data) %>%
+    dplyr::first()
+
+  expected_out <- tibble::tribble(
+    ~"study_id",~"extra_data", ~"new_col1", ~"new_col2",
+    1, 1, "Red", "Green",
+    2, 2, "Multiple", "Green",
+    3, 3, NA, NA
+  ) %>%
+    mutate(
+      new_col1 = factor(new_col1, levels = c("Red", "Yellow", "Blue", "Multiple")),
+      new_col2 = factor(new_col2, levels = c("Green", "Multiple"))
+    )
+
+  expect_equal(out, expected_out)
+})
+
+test_that("combine_checkboxes works for multiple checkbox fields with logicals", {
+  out <- combine_checkboxes(
+    supertbl = supertbl,
+    tbl = "nonrepeat_instrument",
+    cols = c(starts_with("multi")| starts_with("single_checkbox")),
+    values_to = c("new_col1", "new_col2"),
+    keep = FALSE
+  ) %>%
+    pull(redcap_data) %>%
+    dplyr::first()
+
+  expected_out <- tibble::tribble(
+    ~"study_id",~"extra_data", ~"new_col1", ~"new_col2",
+    1, 1, "Red", "Green",
+    2, 2, "Multiple", "Green",
+    3, 3, NA, NA
+  ) %>%
+    mutate(
+      new_col1 = factor(new_col1, levels = c("Red", "Yellow", "Blue", "Multiple")),
+      new_col2 = factor(new_col2, levels = c("Green", "Multiple"))
+    )
+
+  expect_equal(out, expected_out)
+})