diff --git a/.gitignore b/.gitignore
index 52ef87d58a7..6e4ca6e2c6f 100644
--- a/.gitignore
+++ b/.gitignore
@@ -99,6 +99,9 @@ geoip/GeoIP.conf
 geoip/*.mmdb
 geoip/.geoipupdate.lock
 
+# hard stop version tracking
+.sentry-hard-stop
+
 # integration testing
 _integration-test/custom-ca-roots/nginx/*
 sentry/test-custom-ca-roots.py
diff --git a/hard-stop.json b/hard-stop.json
new file mode 100644
index 00000000000..d05ef7ee837
--- /dev/null
+++ b/hard-stop.json
@@ -0,0 +1,13 @@
+{
+    "hard_stops": [
+        "9.1.2",
+        "21.5.0",
+        "21.6.3",
+        "23.6.2",
+        "23.11.0",
+        "24.8.0",
+        "25.5.1",
+        "26.5.0",
+        "26.7.0"
+    ]
+}
diff --git a/install.sh b/install.sh
index c0ead4943b6..76f2ce18bb3 100755
--- a/install.sh
+++ b/install.sh
@@ -21,6 +21,7 @@ source install/dc-detect-version.sh
 source install/error-handling.sh
 # We set the trap at the top level so that we get better tracebacks.
 trap_with_arg cleanup ERR INT TERM EXIT
+source install/check-hard-stop.sh
 source install/check-latest-commit.sh
 source install/check-minimum-requirements.sh
 
diff --git a/install/check-hard-stop.sh b/install/check-hard-stop.sh
new file mode 100644
index 00000000000..b63cb766bfd
--- /dev/null
+++ b/install/check-hard-stop.sh
@@ -0,0 +1,129 @@
+# The idea of this file is to prevent users from skipping a hard stop.
+# This is done by creating a file in /var/run/sentry-hard-stop (or anything set
+# in HARD_STOP_FILE) and checking for its existence before. If the file exists,
+# we assume (and trust) that it's the latest version of the self-hosted sentry
+# version, and no further check (git tag, values on `.env` ) would be done.
+# Otherwise, we assume either this is the first installation, or the first
+# time after this file is being written, and write into that file (by reading
+# either the Git tag or values on `.env` or `.env.custom`).
+#
+# If the "reading" part fails anyway, we would skip this process and continue
+# with the installation.
+#
+# If the user skipped a hard stop, we would halt the installation (or maybe,
+# cancel it altogether), and ask for confirmation.
+#
+# This bit is written by a human.
+
+echo "${_group}Checking for hard stop ... "
+
+# This should be a bash array string, and should be equivalent with the list
+# on https://develop.sentry.dev/self-hosted/releases/#hard-stops
+mapfile -t hard_stops < <(cat hard-stop.json | $jq -r '.hard_stops[]')
+
+# Acquire the new version. This is done by reading `.env` / `.env.custom`
+# for Docker image tags; or by reading the Git tag for the current commit
+declare new_version=""
+# if `.env.custom` exists, prioritize it over `.env`
+if [[ -f ".env.custom" ]]; then
+  new_version=$(grep -E '^SENTRY_IMAGE=' .env.custom | sed 's/^.*=//' | cut -d: -f2 || true)
+fi
+
+if [[ -z "$new_version" ]]; then
+  new_version=$(grep -E '^SENTRY_IMAGE=' .env | sed 's/^.*=//' | cut -d: -f2 || true)
+fi
+
+if [[ -z "$new_version" ]]; then
+  # Check whether `git` exists as a command, and `.git` directory exists
+  if [[ -n "$(command -v git)" ]] && [[ -d "../.git" || -d "./.git" ]]; then
+    # Get the latest tag from the repository
+    new_version=$(git describe --tags --abbrev=0)
+  fi
+fi
+
+# If the `new_version` is still empty, we emit a warning that
+# they're on their own
+if [[ -z "$new_version" ]]; then
+  echo "--------------------------------------------------------------------------------"
+  echo
+  echo "WARNING: Could not determine the new version of the self-hosted Sentry"
+  echo "to perform a hard stop check. Assuming you know what you're doing. Good luck."
+  echo
+  echo "--------------------------------------------------------------------------------"
+fi
+
+# If the `new_version` is empty, we cannot perform any hard stop check.
+# This means the version detection failed across all methods. We already
+# warned the user above, so we skip the check and continue with the installation.
+if [[ -z "$new_version" ]]; then
+  echo "Skipping hard stop check: unable to determine the new version."
+elif [[ "$new_version" == "nightly" ]]; then
+  # If the `new_version` is nightly, we emit a different warning.
+  # This is for fun.
+  echo "--------------------------------------------------------------------------------"
+  echo
+  echo "WARNING: Hello, dear brave traveler. You are installing the nightly version."
+  echo "The hard stop check is skipped for this version. We wish you a safe journey."
+  echo "Good luck."
+  echo
+  echo "--------------------------------------------------------------------------------"
+elif [[ "${#new_version}" -gt 7 ]]; then
+  # Invalid CalVer format. This might be an e2e test, or a user-provided version.
+  echo "--------------------------------------------------------------------------------"
+  echo
+  echo "WARNING: Could not determine the new version of the self-hosted Sentry"
+  echo "to perform a hard stop check due to invalid CalVer format."
+  echo "Assuming you know what you're doing. Good luck."
+  echo
+  echo "--------------------------------------------------------------------------------"
+else
+  # We use snuba image because we don't rebuild the image, and it preserves
+  current_version=$($dc images --format json | $jq -r 'first(.[] | select(.Repository == "ghcr.io/getsentry/snuba")) | .Tag')
+
+  for hard_stop in "${hard_stops[@]}"; do
+    # Let's say we have 3 variables in play here:
+    #   current_version: 24.8.0
+    #   new_version: 26.8.0
+    #   hard_stop: 25.5.1
+    # We don't want to allow the installation to continue if the hard stop is
+    # greater than the new version. So the comparison logic here is:
+    #
+    #   if hard_stop > current_version:
+    #     Check if new_version > hard_stop
+    #     if new_version > hard_stop:
+    #       User is NOT on the right track, they're skipping a hard stop.
+    #       We should give them the warning prompt.
+    #     else:
+    #       User is on the right track.
+    #       continue
+
+    # the version in the image tag.
+    # We also need to handle if those 3 variables are the same, because we
+    # don't want to skip the hard stop if the new version is the same as the
+    # hard stop.
+    if [[ "$current_version" == "$new_version" ]]; then
+      break
+    elif vergte "$hard_stop" "$current_version"; then
+      if vergte "$new_version" "$hard_stop"; then
+        echo "--------------------------------------------------------------------------------"
+        echo
+        echo "WARNING: Your new version ($new_version) will skip a required hard stop of $hard_stop."
+        echo "It is recommended to stop the current installation, and go through the hard stop first."
+        echo "Otherwise, you may encounter unexpected behaviors, such as migration failures, or data loss."
+        echo
+        echo "For future reference, please visit https://develop.sentry.dev/self-hosted/releases/#hard-stops"
+        echo
+        echo "Do you wish to continue? [y/N]"
+        read -r confirmation
+
+        if [[ "$confirmation" != "y" ]]; then
+          echo "Canceled. 😅"
+          exit 1
+        fi
+    fi
+
+    # NO BREAK HERE — keep looping to check remaining hard stops
+  done
+fi
+
+echo "${_endgroup}"
diff --git a/install/error-handling.sh b/install/error-handling.sh
index 040c2a9e252..a94e8378c02 100644
--- a/install/error-handling.sh
+++ b/install/error-handling.sh
@@ -7,6 +7,7 @@ fi
 $dbuild -t sentry-self-hosted-jq-local --platform="$DOCKER_PLATFORM" jq
 
 jq="$CONTAINER_ENGINE run --rm -i sentry-self-hosted-jq-local"
+gh="$CONTAINER_ENGINE run --rm -i docker.io/serversideup/github-cli:alpine"
 sentry_cli="$CONTAINER_ENGINE run --rm -v /tmp:/work -e SENTRY_DSN=$SENTRY_DSN getsentry/sentry-cli"
 DEFAULT_BREADCRUMB_LINE_LIMIT=200