diff --git a/NEWS.md b/NEWS.md
index aa54a18e5..3e3978424 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -8,6 +8,8 @@
 * feat: `benchmark_grid()` will now throw a warning if you mix different predict types in the
   design (#1273).
 * feat: Converting a `BenchmarkResult` to a `data.table` now includes the `task_id`, `learner_id`, and `resampling_id` columns (#1275).
+* fix: Instantiating (repeated) CV on tasks with observations less than the
+number of folds now fails.
 
 # mlr3 0.23.0
 
diff --git a/R/Resampling.R b/R/Resampling.R
index 6cf54d97d..2986a7b58 100644
--- a/R/Resampling.R
+++ b/R/Resampling.R
@@ -170,6 +170,7 @@ Resampling = R6Class("Resampling",
     #' the object in its previous state.
     instantiate = function(task) {
       task = assert_task(as_task(task))
+      private$.check(task)
       strata = task$strata
       groups = task$groups
 
@@ -257,6 +258,9 @@ Resampling = R6Class("Resampling",
     .id = NULL,
     .hash = NULL,
     .groups = NULL,
+    .check = function(task) {
+      TRUE
+    },
 
     .get_set = function(getter, i) {
       if (!self$is_instantiated) {
diff --git a/R/ResamplingCV.R b/R/ResamplingCV.R
index 34a0e60fc..9922b492d 100644
--- a/R/ResamplingCV.R
+++ b/R/ResamplingCV.R
@@ -61,12 +61,25 @@ ResamplingCV = R6Class("ResamplingCV", inherit = Resampling,
 
   private = list(
     .sample = function(ids, ...) {
+      pvs = self$param_set$get_values()
       data.table(
         row_id = ids,
-        fold = shuffle(seq_along0(ids) %% as.integer(self$param_set$values$folds) + 1L),
+        fold = shuffle(seq_along0(ids) %% as.integer(pvs$folds) + 1L),
         key = "fold"
       )
     },
+    .check = function(task) {
+      pvs = self$param_set$get_values()
+      if (!is.null(task$groups)) {
+        n_groups = length(unique(task$groups$group))
+        if (n_groups < pvs$folds) {
+          stopf("Cannot instantiate ResamplingCV with %i folds on a grouped task with %i groups.", pvs$folds, n_groups)
+        }
+      }
+      if (task$nrow < pvs$folds) {
+        stopf("Cannot instantiate ResamplingCV with %i folds on a task with %i rows.", pvs$folds, task$nrow)
+      }
+    },
 
     .get_train = function(i) {
       self$instance[!list(i), "row_id", on = "fold"][[1L]]
diff --git a/R/ResamplingRepeatedCV.R b/R/ResamplingRepeatedCV.R
index bbf3b492c..d27ee43e4 100644
--- a/R/ResamplingRepeatedCV.R
+++ b/R/ResamplingRepeatedCV.R
@@ -93,13 +93,25 @@ ResamplingRepeatedCV = R6Class("ResamplingRepeatedCV", inherit = Resampling,
 
   private = list(
     .sample = function(ids, ...) {
-      pv = self$param_set$values
+      pv = self$param_set$get_values()
       n = length(ids)
       folds = as.integer(pv$folds)
       map_dtr(seq_len(pv$repeats), function(i) {
         data.table(row_id = ids, rep = i, fold = shuffle(seq_len0(n) %% folds + 1L))
       })
     },
+    .check = function(task) {
+      pvs = self$param_set$get_values()
+      if (!is.null(task$groups)) {
+        n_groups = length(unique(task$groups$group))
+        if (n_groups < pvs$folds) {
+          stopf("Cannot instantiate ResamplingRepeatedCV with %i folds on a grouped task with %i groups.", pvs$folds, n_groups)
+        }
+      }
+      if (task$nrow < pvs$folds) {
+        stopf("Cannot instantiate ResamplingRepeatedCV with %i folds on a task with %i rows.", pvs$folds, task$nrow)
+      }
+    },
 
     .get_train = function(i) {
       i = as.integer(i) - 1L
diff --git a/tests/testthat/test_Resampling.R b/tests/testthat/test_Resampling.R
index db7f67d7b..38076622f 100644
--- a/tests/testthat/test_Resampling.R
+++ b/tests/testthat/test_Resampling.R
@@ -158,3 +158,17 @@ test_that("task_row_hash in Resampling works correctly", {
   resampling$instantiate(task)
   expect_identical(resampling$task_row_hash, task$row_hash)
 })
+
+test_that("folds must be <= task size", {
+  cv = rsmp("cv", folds = 151)
+  rep_cv = rsmp("repeated_cv", folds = 151)
+  task = tsk("iris")
+  expect_error(cv$instantiate(task), "Cannot instantiate ResamplingCV with 151 folds on a task with 150 rows")
+  expect_error(rep_cv$instantiate(task), "Cannot instantiate ResamplingRepeatedCV with 151 folds on a task with 150 rows")
+
+  task$col_roles$group = "Species"
+  cv$param_set$set_values(folds = 4L)
+  rep_cv$param_set$set_values(folds = 4L)
+  expect_error(cv$instantiate(task), "on a grouped task with 3 groups")
+  expect_error(rep_cv$instantiate(task), "on a grouped task with 3 groups")
+})