diff --git a/scripts/update_tests.sh b/scripts/update_tests.sh
new file mode 100755
index 0000000000..ff65c7216b
--- /dev/null
+++ b/scripts/update_tests.sh
@@ -0,0 +1,319 @@
+#!/bin/bash
+
+usage() {
+    cat >&2 <<EOF
+Usage: $0 [OPTIONS]
+
+Copy tests from CPython to RustPython.
+Optionally copy untracked tests, and dynamic annotation of failures.
+This updater is not meant to be used as a standalone updater. Care needs to be taken to review everything done
+
+Options:
+  -c/--cpython-path <path>   Path to the CPython source tree (older version)
+  -r/--rpython-path <path>   Path to the RustPython source tree (newer version)
+  -s/--update-skipped        Update existing skipped tests (must be run separate from updating the tests)
+  -a/--annotate              While copying tests, run them and annotate failures dynamically
+  -u/--copy-untracked        Copy untracked tests
+  -t/--timeout               Set a timeout for a test
+  -j/--jobs                  How many libraries can be processed at a time
+  -h/--help                  Show this help message and exit
+
+Example Usage: 
+$0 -c ~/cpython -r . -t 300   # Updates all non-updated tests with a timeout value of 300 seconds
+$0 -c ~/cpython -r . -u -j 5    # Updates all non-updated tests + copies files not in cpython into rpython, with maximum 5 processes active at a time
+$0 -c ~/cpython -r . -a         # Updates all non-updated tests + annotates with @unittest.expectedFailure/@unittest.skip
+$0 -r . -s                      # For all current tests, check if @unittest.skip can be downgraded to @unittest.expectedFailure
+
+*Notes:
+    * When using the update skip functionality
+        * Updating only looks for files with the format "test_*.py". Everything else (including __init__.py and __main__.py files are ignored)
+**Known limitations:
+    * In multithreaded tests, if the tests are orphaned, then the updater can deadlock, as threads can accumulate and block the semaphore
+    * The updater does not add skips to classes, only on tests
+    * If there are multiple tests with the same name, a decorator will be added to all of them
+    * The updater does not retain anything more specific than a general skip (skipIf/Unless will be replaced by a general skip)
+    * Currently, the updater does not take unexpected successes into account
+
+EOF
+    exit 1
+}
+
+if [[ $# -eq 0 ]]; then
+    usage 
+fi
+
+
+cpython_path=""
+rpython_path=""
+copy_untracked=false
+annotate=false
+timeout=300
+check_skip_flag=false
+num_jobs=20
+libraries=()
+ignored_libraries=("multiprocessing" "concurrent")
+
+while [[ $# -gt 0 ]]; do
+    case "$1" in
+        -c|--cpython-path)
+            cpython_path="$2/Lib/test"
+            shift 2
+            ;;
+        -r|--rpython-path)
+            rpython_path="$2/Lib/test"
+            shift 2
+            ;;
+        -u|--copy-untracked)
+            copy_untracked=true
+            shift
+            ;;
+        -h|--help)
+            usage
+            exit 1
+            ;;
+        -s|--update-skipped)
+            check_skip_flag=true
+            shift
+            ;;
+        -t|--timeout)
+            timeout="$2"
+            shift 2
+            ;;
+        -a|--annotate)
+            annotate=true
+            shift
+            ;;
+        -j|--jobs)
+            num_jobs="$2"
+            shift 2
+            ;;
+        *)
+            libraries+=("$1")
+            shift
+            ;;
+    esac
+done
+# -------------------------------------- Constants ------------------------------------- #
+RUSTPYTHON_POSSIBLE_SKIP_RE="@unittest.skip.*\([\"']TODO:\s*RUSTPYTHON.*[\"']\)"
+RUSTPYTHON_CANONICAL_SKIP_RE="@unittest.skip\('TODO: RUSTPYTHON; .*'\)"
+RUSTPYTHON_CANONICAL_EX_FAILURE="@unittest.expectedFailure # TODO: RUSTPYTHON"
+RUSTPYTHON_CANONICAL_EX_FAILURE_RE="\s@unittest\.expectedFailure # TODO: RUSTPYTHON.*"
+
+# --------------------------------- Updating functions --------------------------------- #
+
+update_tests() {
+    local libraries=("$@")
+    for lib in "${libraries[@]}"
+    do 
+        sem
+        update_test "$lib" &
+    done
+    wait
+}
+
+update_test() {
+    local lib=$1
+    local clib_path="$cpython_path/$lib"
+    local rlib_path="$rpython_path/$lib"
+
+    if [[ -f "$clib_path" && -f "$rlib_path" ]] && files_equal "$clib_path" "$rlib_path"; then
+        echo "No changes in $lib. Skipping..." 
+        return
+    fi
+
+    if [[ ! -f "$rlib_path" ]]; then
+        echo "Test file $lib missing"
+        if $copy_untracked; then
+            echo "Copying $lib ..."
+            cp "$clib_path" "$rlib_path"
+        fi
+    else
+        echo "Using lib_updater to update $lib"
+        ./scripts/lib_updater.py --from $clib_path --to $rlib_path -o $rlib_path
+    fi
+
+
+    if [[ $annotate && -f "$rlib_path" && $(basename -- "$rlib_path") == test_*.py ]]; then
+        annotate_lib $lib $rlib_path
+    fi
+}
+
+# --------------------------------- Downgrade Skips functions --------------------------------- #
+
+check_skips() {
+    local libraries=("$@")
+    for lib in "${libraries[@]}"
+    do
+        if grep -qiE "$RUSTPYTHON_POSSIBLE_SKIP_RE" "$rpython_path/$lib"; then
+            sem
+            check_skip "$lib" &
+        else
+            echo "Skipping $lib" >&2
+        fi
+    done
+    wait
+}
+
+check_skip() {
+    local lib=$1
+    local rlib_path="$rpython_path/$lib"
+
+    remove_skips $rlib_path
+
+    annotate_lib $lib $rlib_path
+}
+
+apply_skip() {
+    local rlib_path=$1
+    local test_name=$2
+    local hanging=$3
+    message="unknown"
+
+    # Check if the test has a backup skip
+    if [[ -n "${SKIP_BACKUP[$test_name]}" ]]; then
+        message="${SKIP_BACKUP[$test_name]//\'/\"}" 
+    elif $hanging; then
+        message="hanging"
+    fi
+
+    add_above_test "$rlib_path" "$test_name" "@unittest.skip('TODO: RUSTPYTHON; $message')"
+}
+
+backup_skips() {
+    local rlib_path=$1
+    declare -gA SKIP_BACKUP=()  # global associative array
+    readarray -t skips < <(grep -E -n "^[[:space:]]*@unittest\.skip.*TODO\s?:\s?RUSTPYTHON" "$rlib_path" | sort -u)
+
+    for line in "${skips[@]}"; do
+        line_num="${line%%:*}"
+        line_text=$(echo "$line" | grep -oPi "(?<=RUSTPYTHON)\s*[;:]\s*\K(.*)?(?=[\"'])")
+        next_line=$(sed -n "$((line_num + 1))p" "$rlib_path")
+
+        if [[ "$next_line" =~ def[[:space:]]+([a-zA-Z0-9_]+)\( ]]; then
+            test_name="${BASH_REMATCH[1]}"
+            SKIP_BACKUP[$test_name]="$line_text"
+        fi
+    done
+}
+
+# --------------------------------- General functions --------------------------------- #
+
+annotate_lib() {
+    local lib=${1//\//.}
+    local rlib_path=$2
+    local output=$(rustpython $lib 2>&1)
+
+    if grep -q "NO TESTS RAN" <<< "$output"; then
+        echo "No tests ran in $lib. skipping annotation"
+        return
+    fi
+    
+    echo "Annotating $lib"
+
+    local attempts=0
+    while ! grep -q "Tests result: SUCCESS" <<< "$output"; do
+        ((attempts++))
+        # echo "$lib failing, annotating..."
+        readarray -t failed_tests <<< "$(echo "$output" | awk '/^(FAIL:|ERROR:)/ {print $2}' | sort -u)"
+        
+        # If the test fails/errors, then expectedFailure it
+        for test in "${failed_tests[@]}"
+        do
+            if already_failed $rlib_path $test; then
+                replace_expected_with_skip $rlib_path $test
+            else
+                add_above_test $rlib_path $test "$RUSTPYTHON_CANONICAL_EX_FAILURE" 
+            fi
+        done
+
+        # If the test crashes/hangs, then skip it
+        if grep -q "\.\.\.$" <<< "$output"; then
+            crashing_test=$(echo "$output" | grep '\.\.\.$' | head -n 1 | awk '{print $1}')
+            if grep -q "Timeout" <<< "$output"; then
+                hanging=true
+            else
+                hanging=false
+            fi
+            apply_skip "$rlib_path" "$crashing_test" $hanging
+        fi
+
+        output=$(rustpython $lib 2>&1)
+
+        if [[ $attempts -gt 15 ]]; then 
+            echo "Issue annotating $lib" >&2
+            return;
+        fi
+    done
+    echo "Successfully updated $lib"
+
+    unset SKIP_BACKUP
+}
+
+sem() {
+    while (( $(jobs -rp | wc -l) >= $num_jobs )); do
+        sleep 0.1  # brief pause before checking again
+    done
+}
+
+add_above_test() {
+    local file=$1
+    local test=$2
+    local line=$3
+    sed -i "s/^\([[:space:]]*\)def $test(/\1$line\n\1def $test(/" "$file"
+}
+
+# --------------------------------- Utility functions --------------------------------- #
+
+rustpython() {
+    cargo run --release --features encodings,sqlite -- -m test -j 1 -u all --fail-env-changed --timeout "$timeout" -v "$@"
+}
+
+replace_expected_with_skip() {
+    file=$1
+    test_name=$2
+    sed -E "/$RUSTPYTHON_CANONICAL_EX_FAILURE_RE/ { N; /\n\s*def $test_name/ { s/^(\s*)@unittest\.expectedFailure\s+# TODO: RUSTPYTHON/\1@unittest.skip\('TODO: RUSTPYTHON'\)/ } }" -i $file
+}
+
+already_failed() {
+    file=$1
+    test_name=$2
+    grep -qPz "$RUSTPYTHON_CANONICAL_EX_FAILURE_RE\n\s*def\s+${test_name}\(" $file
+}
+
+files_equal() {
+    cmp --silent "$1" "$2"
+}
+
+
+remove_skips() {
+    local rlib_path=$1
+
+    echo "Removing all skips from $rlib_path"
+
+    backup_skips "$rlib_path"
+
+    sed -i -E '/^[[:space:]]*@unittest\.skip.*\(["'\'']TODO\s?:\s?RUSTPYTHON.*["'\'']\)/Id' $rlib_path
+}
+
+main() {
+    if ! $check_skip_flag; then
+        echo "Updating Tests"
+
+        # If libraries are not specified, then update all tests
+        if [[ "${#libraries[@]}" -eq 0 ]]; then
+            readarray -t libraries <<< $(find ${cpython_path} -type f -printf "%P\n" | grep -vE "$(IFS=\|; echo "${ignored_libraries[*]}")")
+        fi
+        update_tests "${libraries[@]}"
+    else
+        echo "Checking Skips"
+
+        # If libraries are not specified, then check all tests
+        if [[ ${#libraries[@]} -eq 0 ]]; then
+            readarray -t libraries <<< $(find ${rpython_path} -iname "test_*.py" -type f -printf "%P\n" | grep -vE "$(IFS=\|; echo "${ignored_libraries[*]}")")
+        fi
+        check_skips "${libraries[@]}"
+    fi
+}
+
+
+main
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