diff --git a/NEWS.md b/NEWS.md
index 4e108fae47..8c3693dbc4 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -155,6 +155,8 @@
 
 6. `DT[subset]` where `DT[(subset)]` or `DT[subset==TRUE]` was intended; i.e., subsetting by a logical column whose name conflicts with an existing function, now gives a friendlier error message, [#5014](https://github.com/Rdatatable/data.table/issues/5014). Thanks @michaelchirico for the suggestion and PR, and @ColeMiller1 for helping with the fix.
 
+7. Grouping by a `list` column has its error message improved stating this is unsupported, [#4308](https://github.com/Rdatatable/data.table/issues/4308). Thanks @sindribaldur for filing, and @michaelchirico for the PR. Please add your vote and especially use cases to the [#1597](https://github.com/Rdatatable/data.table/issues/1597) feature request.
+
 
 # data.table [v1.14.0](https://github.com/Rdatatable/data.table/milestone/23?closed=1)  (21 Feb 2021)
 
diff --git a/R/data.table.R b/R/data.table.R
index 85f1d9edb3..392599da71 100644
--- a/R/data.table.R
+++ b/R/data.table.R
@@ -881,7 +881,9 @@ replace_dot_alias = function(e) {
         if (!is.list(byval)) stop("'by' or 'keyby' must evaluate to a vector or a list of vectors (where 'list' includes data.table and data.frame which are lists, too)")
         if (length(byval)==1L && is.null(byval[[1L]])) bynull=TRUE #3530 when by=(function()NULL)()
         if (!bynull) for (jj in seq_len(length(byval))) {
-          if (!typeof(byval[[jj]]) %chin% ORDERING_TYPES) stop("column or expression ",jj," of 'by' or 'keyby' is type ",typeof(byval[[jj]]),". Do not quote column names. Usage: DT[,sum(colC),by=list(colA,month(colB))]")
+          if (!(this_type <- typeof(byval[[jj]])) %chin% ORDERING_TYPES) {
+            stop(gettextf("Column or expression %d of 'by' or 'keyby' is type '%s' which is not currently supported. If you have a compelling use case, please add it to https://github.com/Rdatatable/data.table/issues/1597. As a workaround, consider converting the column to a supported type, e.g. by=sapply(list_col, toString), whilst taking care to maintain distinctness in the process.", jj, this_type))
+          }
         }
         tt = vapply_1i(byval,length)
         if (any(tt!=xnrow)) stop(domain=NA, gettextf("The items in the 'by' or 'keyby' list are length(s) (%s). Each must be length %d; the same length as there are rows in x (after subsetting if i is provided).", paste(tt, collapse=","), xnrow))
diff --git a/inst/tests/tests.Rraw b/inst/tests/tests.Rraw
index 41f8978b17..5b21448fa6 100644
--- a/inst/tests/tests.Rraw
+++ b/inst/tests/tests.Rraw
@@ -14086,7 +14086,9 @@ test(1984.05, DT[ , sum(b), keyby = c, verbose = TRUE],
 ### hitting byval = eval(bysub, setattr(as.list(seq_along(xss)), ...)
 test(1984.06, DT[1:3, sum(a), by=b:c], data.table(b=10:8, c=1:3, V1=1:3))
 test(1984.07, DT[, sum(a), by=call('sin',pi)], error='must evaluate to a vector or a list of vectors')
-test(1984.08, DT[, sum(a), by=as.raw(0)],           error='column or expression.*type raw')
+test(1984.081, DT[, sum(a), by=as.raw(0)],     error="Column or expression.*1.*type 'raw'.*not.*supported")
+test(1984.082, data.table(A=1:4, L=list(1, 1:2, 1, 1:3), V=1:4)[, sum(V), by=.(A,L)],  # better error message, 4308
+               error="Column or expression.*2.*type 'list'.*not.*supported")
 test(1984.09, DT[, sum(a), by=.(1,1:2)],       error='The items.*list are length[(]s[)] [(]1,2[)].*Each must be length 10; .*rows in x.*after subsetting')
 options('datatable.optimize' = Inf)
 test(1984.10, DT[ , 1, by = .(a %% 2), verbose = TRUE],