diff --git a/.gitignore b/.gitignore
index abc49402887..e6daa2c5ce3 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,3 +1,6 @@
+# Error reporting choice cache
+.reporterrors
+
 # Byte-compiled / optimized / DLL files
 __pycache__/
 *.py[cod]
diff --git a/install.sh b/install.sh
index efee0cdf32e..5eed8419f2b 100755
--- a/install.sh
+++ b/install.sh
@@ -1,5 +1,5 @@
 #!/usr/bin/env bash
-set -e
+set -eE
 
 # Pre-pre-flight? 🤷
 if [[ -n "$MSYSTEM" ]]; then
@@ -14,6 +14,8 @@ source parse-cli.sh
 source detect-platform.sh
 source dc-detect-version.sh
 source 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 check-latest-commit.sh
 source check-minimum-requirements.sh
 
diff --git a/install/error-handling.sh b/install/error-handling.sh
index 9121bba89eb..74793a2bb80 100644
--- a/install/error-handling.sh
+++ b/install/error-handling.sh
@@ -1,23 +1,112 @@
 echo "${_group}Setting up error handling ..."
 
+export SENTRY_DSN='https://19555c489ded4769978daae92f2346ca@self-hosted.getsentry.net/3'
+export SENTRY_ORG=self-hosted
+export SENTRY_PROJECT=installer
+export REPORT_ERRORS=0
+
+function send_event {
+  local sentry_cli="docker run --rm -v $basedir:/work -e SENTRY_ORG=$SENTRY_ORG -e SENTRY_PROJECT=$SENTRY_PROJECT -e SENTRY_DSN=$SENTRY_DSN getsentry/sentry-cli"
+  command pushd .. > /dev/null
+  $sentry_cli send-event --no-environ -f "$1" -m "$2" --logfile $log_file
+  command popd > /dev/null
+}
+
+reporterrors="$basedir/.reporterrors"
+if [[ -f $reporterrors ]]; then
+  echo -n "Found a .reporterrors file. What does it say? "
+  cat $reporterrors
+  if [[ "$(cat $reporterrors)" == "yes" ]]; then
+    export REPORT_ERRORS=1
+  else
+    export REPORT_ERRORS=0
+  fi
+else
+  echo
+  echo "Hey, so ... we would love to find out when you hit an issue with this here"
+  echo "installer you are running. Turns out there is an app for that, called Sentry."
+  echo "Are you okay with us sending info to Sentry when you run this installer?"
+  echo
+  echo "  y / yes / 1"
+  echo "  n / no / 0"
+  echo
+  echo "(Btw, we send this to our own self-hosted Sentry instance, not to Sentry SaaS,"
+  echo "so that we can be in this together.)"
+  echo
+  echo "Here's the info we may collect in order to help us improve the installer:"
+  echo
+  echo "  - OS username"
+  echo "  - IP address"
+  echo "  - install log"
+  echo "  - performance data"
+  echo
+  echo "Thirty (30) day retention. No marketing. Privacy policy at sentry.io/privacy."
+  echo
+
+  yn=""
+  until [ ! -z "$yn" ]
+  do
+    read -p "y or n? " yn
+    case $yn in
+      y | yes | 1) export REPORT_ERRORS=1; echo "yes" > $reporterrors; echo; echo -n "Thank you.";;
+      n | no | 0) export REPORT_ERRORS=0; echo "no" > $reporterrors; echo; echo -n "Understood.";;
+      *) yn="";;
+    esac
+  done
+
+  echo " Your answer is cached in '.reporterrors', remove it to see this"
+  echo "prompt again."
+  echo
+  sleep 5
+fi
+
+# Make sure we can use sentry-cli if we need it.
+if [ "$REPORT_ERRORS" == 1 ]; then
+  if ! docker pull getsentry/sentry-cli:latest; then
+    echo "Failed to pull sentry-cli, won't report errors after all."
+    export REPORT_ERRORS=0
+  fi;
+fi;
+
 # Courtesy of https://stackoverflow.com/a/2183063/90297
 trap_with_arg() {
   func="$1" ; shift
   for sig ; do
-    trap "$func $sig "'$LINENO' "$sig"
+    trap "$func $sig" "$sig"
   done
 }
 
 DID_CLEAN_UP=0
 # the cleanup function will be the exit point
 cleanup () {
+  local retcode=$?
+  local cmd="${BASH_COMMAND}"
   if [[ "$DID_CLEAN_UP" -eq 1 ]]; then
     return 0;
   fi
   DID_CLEAN_UP=1
-
   if [[ "$1" != "EXIT" ]]; then
-    echo "An error occurred, caught SIG$1 on line $2";
+    set +o xtrace
+    printf -v err '%s' "Error in ${BASH_SOURCE[1]}:${BASH_LINENO[0]}."
+    printf -v cmd_exit '%s' "'$cmd' exited with status $retcode"
+    printf '%s\n%s\n' "$err" "$cmd_exit"
+    local stack_depth=${#FUNCNAME[@]}
+    local traceback=""
+    if [ $stack_depth -gt 2 ]; then
+      for ((i=$(($stack_depth - 1)),j=1;i>0;i--,j++)); do
+          local indent="$(yes a | head -$j | tr -d '\n')"
+          local src=${BASH_SOURCE[$i]}
+          local lineno=${BASH_LINENO[$i-1]}
+          local funcname=${FUNCNAME[$i]}
+          printf -v traceback '%s\n' "$traceback${indent//a/-}> $src:$funcname:$lineno"
+      done
+    fi
+    echo "$traceback"
+
+    if [ "$REPORT_ERRORS" == 1 ]; then
+      local traceback_hash=$(echo -n $traceback | docker run --rm busybox md5sum | cut -d' ' -f1)
+      send_event "$traceback_hash" "$cmd_exit"
+    fi
 
     if [[ -n "$MINIMIZE_DOWNTIME" ]]; then
       echo "*NOT* cleaning up, to clean your environment run \"docker compose stop\"."
@@ -30,6 +119,5 @@ cleanup () {
     $dc stop -t $STOP_TIMEOUT &> /dev/null
   fi
 }
-trap_with_arg cleanup ERR INT TERM EXIT
 
 echo "${_endgroup}"
diff --git a/integration-test.sh b/integration-test.sh
index 52421e8f495..244ca2da7ea 100755
--- a/integration-test.sh
+++ b/integration-test.sh
@@ -4,6 +4,7 @@ set -ex
 echo "Reset customizations"
 rm -f sentry/enhance-image.sh
 rm -f sentry/requirements.txt
+echo no > .reporterrors
 
 echo "Testing initial install"
 ./install.sh