diff --git a/e2e/tests-dfx/upgrade_assets_canister.bash b/e2e/tests-dfx/upgrade_assets_canister.bash
new file mode 100644
index 0000000000..b27c3a77ce
--- /dev/null
+++ b/e2e/tests-dfx/upgrade_assets_canister.bash
@@ -0,0 +1,51 @@
+#!/usr/bin/env bats
+
+load ../utils/_
+load ../utils/releases
+
+setup() {
+    standard_setup
+
+    dfx_new
+}
+
+teardown() {
+    dfx_stop
+
+    standard_teardown
+}
+
+# The e2e matrix should ensure that this test is not run on ic-ref, as the Wasm does
+# heavy computation
+@test "asset canister can be upgraded from the latest release version when storing a lot of data" {
+    # As a starting point for the load, we looked at OpenChat's usage.
+    # As of 2023-02-10, they had 40MB of assets spread over 135 files.
+    # We'll use a bigger example (~3x in number of files, ~20x in total size) to add a safety margin.
+    local -r total_files=400
+    local file_size
+    if [ "$(uname)" == "Darwin" ]; then
+        file_size="2m"
+    else
+        file_size="2M"
+    fi
+
+    local -r canister_name=e2e_project_frontend
+
+    local -r asset_dir="src/${canister_name}/assets"
+    for a in $(seq 1 $total_files); do
+        dd if=/dev/urandom of="${asset_dir}/large-asset-${a}.bin" bs="$file_size" count=1 1>/dev/null
+    done
+
+    dfx_start
+    dfx canister create --all
+    dfx build
+
+    # Install the canister using the Wasm from the latest release
+    local -r release_asset_wasm_dir=$(mktemp -d)
+    get_from_latest_release_tarball src/distributed/assetstorage.wasm.gz "$release_asset_wasm_dir"
+    export DFX_ASSETS_WASM="${release_asset_wasm_dir}/assetstorage.wasm.gz"
+    assert_command dfx canister install $canister_name
+
+    use_default_asset_wasm
+    assert_command dfx deploy $canister_name --upgrade-unchanged
+}
diff --git a/e2e/utils/releases.bash b/e2e/utils/releases.bash
new file mode 100644
index 0000000000..3e93efd781
--- /dev/null
+++ b/e2e/utils/releases.bash
@@ -0,0 +1,26 @@
+# Print the latest dfx version available on GitHub releases
+get_latest_dfx_version() {
+    latest_version=$(curl -sL --retry 5 --retry-all-errors "https://api.github.com/repos/dfinity/sdk/releases/latest" | jq -r ".tag_name")
+    echo "$latest_version"
+}
+
+# Extract a particular file from the latest release tarball, and save it to the specified destination
+# Usage: get_from_latest_release_tarball <file_path> <destination>
+get_from_latest_release_tarball() {
+    local -r file_path=$1
+    local -r destination=$2
+    local -r tarball_url=$(curl -sL --retry 5 --retry-all-errors "https://api.github.com/repos/dfinity/sdk/releases/latest" | jq -r ".tarball_url")
+
+    local -r temp_dir=$(mktemp -d)
+    curl -sL --retry 5 --retry-all-errors "$tarball_url" -o "${temp_dir}/release.tar.gz" || (echo "It's really curl that failed" && return 1)
+
+    if [ "$(uname)" == "Darwin" ]; then
+        tar -xzf "$temp_dir/release.tar.gz" -C "$temp_dir" "*/$file_path"
+    elif [ "$(uname)" == "Linux" ]; then
+        tar -xzf "$temp_dir/release.tar.gz" -C "$temp_dir" --wildcards "*/$file_path"
+    fi
+
+    local -r file_name=$(basename "$file_path")
+    local -r extracted_file=$(find "$temp_dir" -type f -name "$file_name")
+    mv "$extracted_file" "$destination"
+}
diff --git a/scripts/workflows/e2e-matrix.py b/scripts/workflows/e2e-matrix.py
index 8c894a6dad..5b9becd6d2 100755
--- a/scripts/workflows/e2e-matrix.py
+++ b/scripts/workflows/e2e-matrix.py
@@ -27,6 +27,7 @@ def test_scripts(prefix):
         {"backend": "ic-ref", "test": "dfx/new"},
         {"backend": "ic-ref", "test": "dfx/print"},
         {"backend": "ic-ref", "test": "dfx/signals"},
+        {"backend": "ic-ref", "test": "dfx/upgrade_assets_canister"},
     ],
 }