From a1a602aa4423ec12ddba5e97b966543707fc2536 Mon Sep 17 00:00:00 2001
From: datadog-bits <263423550+datadog-bits@users.noreply.github.com>
Date: Mon, 14 Sep 2026 13:13:37 +0000
Subject: [PATCH 1/3] APMSP-3973 Retry Docker SSI Agent install

Co-authored-by: nccatoni <222672590+nccatoni@users.noreply.github.com>
---
 utils/build/ssi/base/download_with_retry.sh   | 23 +++++++++++++++++++
 utils/build/ssi/base/install_script_ssi.sh    |  8 ++++++-
 .../ssi/base/install_script_ssi_installer.sh  |  7 +++++-
 3 files changed, 36 insertions(+), 2 deletions(-)

diff --git a/utils/build/ssi/base/download_with_retry.sh b/utils/build/ssi/base/download_with_retry.sh
index c06e6249595..6c506dace0d 100644
--- a/utils/build/ssi/base/download_with_retry.sh
+++ b/utils/build/ssi/base/download_with_retry.sh
@@ -18,3 +18,26 @@ download_with_retry() {
     echo "[ERROR] ${output} is missing or empty after ${max_attempts} attempts" >&2
     return 1
 }
+
+run_with_retry() {
+    local description="$1"
+    shift
+
+    local max_attempts=3
+    local retry_delay=5
+    local attempt
+    for (( attempt = 1; attempt <= max_attempts; attempt++ )); do
+        echo "[TRACE] running ${description} (attempt ${attempt}/${max_attempts})"
+        if "$@"; then
+            return 0
+        fi
+
+        if (( attempt < max_attempts )); then
+            echo "[WARN] ${description} failed; retrying in ${retry_delay} seconds" >&2
+            sleep "$retry_delay"
+        fi
+    done
+
+    echo "[ERROR] ${description} failed after ${max_attempts} attempts" >&2
+    return 1
+}
diff --git a/utils/build/ssi/base/install_script_ssi.sh b/utils/build/ssi/base/install_script_ssi.sh
index 1bac8e44551..85177432141 100755
--- a/utils/build/ssi/base/install_script_ssi.sh
+++ b/utils/build/ssi/base/install_script_ssi.sh
@@ -54,7 +54,13 @@ if [ ! -s "install_script_agent7.sh" ]; then
     exit 1
 fi
 
-DD_REPO_URL=${DD_injection_repo_url} DD_INSTALL_ONLY=true DD_APM_INSTRUMENTATION_ENABLED=host bash ./install_script_agent7.sh
+run_with_retry \
+    "Datadog Agent installer" \
+    env \
+    "DD_REPO_URL=${DD_injection_repo_url}" \
+    DD_INSTALL_ONLY=true \
+    DD_APM_INSTRUMENTATION_ENABLED=host \
+    bash ./install_script_agent7.sh || exit 1
 
 if [ -f /etc/debian_version ] || [ "$DISTRIBUTION" == "Debian" ] || [ "$DISTRIBUTION" == "Ubuntu" ]; then
     OS="Debian"
diff --git a/utils/build/ssi/base/install_script_ssi_installer.sh b/utils/build/ssi/base/install_script_ssi_installer.sh
index 336bda6ede2..cdd2081302b 100755
--- a/utils/build/ssi/base/install_script_ssi_installer.sh
+++ b/utils/build/ssi/base/install_script_ssi_installer.sh
@@ -5,4 +5,9 @@ source ./download_with_retry.sh
 
 download_with_retry https://dd-agent.s3.amazonaws.com/scripts/install_script_agent7.sh || exit 1
 
-DD_INSTALL_ONLY=true DD_INSTALLER=true bash ./install_script_agent7.sh
+run_with_retry \
+    "Datadog Agent installer" \
+    env \
+    DD_INSTALL_ONLY=true \
+    DD_INSTALLER=true \
+    bash ./install_script_agent7.sh || exit 1

From 98d4eff332df0342a57aa192628abcf5fb18c65c Mon Sep 17 00:00:00 2001
From: datadog-bits <263423550+datadog-bits@users.noreply.github.com>
Date: Mon, 14 Sep 2026 13:25:39 +0000
Subject: [PATCH 2/3] APMSP-3973 Factorize retry helpers

Co-authored-by: nccatoni <222672590+nccatoni@users.noreply.github.com>
---
 utils/build/ssi/base/download_with_retry.sh   | 45 ++++++++++---------
 utils/build/ssi/base/install_script_ssi.sh    |  2 +
 .../ssi/base/install_script_ssi_installer.sh  |  2 +
 3 files changed, 27 insertions(+), 22 deletions(-)

diff --git a/utils/build/ssi/base/download_with_retry.sh b/utils/build/ssi/base/download_with_retry.sh
index 6c506dace0d..a9a9e7dc680 100644
--- a/utils/build/ssi/base/download_with_retry.sh
+++ b/utils/build/ssi/base/download_with_retry.sh
@@ -1,30 +1,11 @@
 #!/bin/bash
 
-download_with_retry() {
-    local url="$1"
-    local output
-    output="$(basename "$url")"
-
-    local max_attempts=5
-    local attempt
-    for (( attempt = 1; attempt <= max_attempts; attempt++ )); do
-        echo "[TRACE] downloading ${output} (attempt ${attempt}/${max_attempts})"
-        if curl --fail --retry 3 -sSL -o "$output" "$url" && [ -s "$output" ]; then
-            return 0
-        fi
-        rm -f "$output"
-    done
-
-    echo "[ERROR] ${output} is missing or empty after ${max_attempts} attempts" >&2
-    return 1
-}
-
 run_with_retry() {
     local description="$1"
-    shift
+    local max_attempts="$2"
+    local retry_delay="$3"
+    shift 3
 
-    local max_attempts=3
-    local retry_delay=5
     local attempt
     for (( attempt = 1; attempt <= max_attempts; attempt++ )); do
         echo "[TRACE] running ${description} (attempt ${attempt}/${max_attempts})"
@@ -41,3 +22,23 @@ run_with_retry() {
     echo "[ERROR] ${description} failed after ${max_attempts} attempts" >&2
     return 1
 }
+
+_download_once() {
+    local url="$1"
+    local output="$2"
+
+    if curl --fail --retry 3 -sSL -o "$output" "$url" && [ -s "$output" ]; then
+        return 0
+    fi
+
+    rm -f "$output"
+    return 1
+}
+
+download_with_retry() {
+    local url="$1"
+    local output
+    output="$(basename "$url")"
+
+    run_with_retry "download ${output}" 5 0 _download_once "$url" "$output"
+}
diff --git a/utils/build/ssi/base/install_script_ssi.sh b/utils/build/ssi/base/install_script_ssi.sh
index 85177432141..5f1ba9f4864 100755
--- a/utils/build/ssi/base/install_script_ssi.sh
+++ b/utils/build/ssi/base/install_script_ssi.sh
@@ -56,6 +56,8 @@ fi
 
 run_with_retry \
     "Datadog Agent installer" \
+    3 \
+    5 \
     env \
     "DD_REPO_URL=${DD_injection_repo_url}" \
     DD_INSTALL_ONLY=true \
diff --git a/utils/build/ssi/base/install_script_ssi_installer.sh b/utils/build/ssi/base/install_script_ssi_installer.sh
index cdd2081302b..3d823f72150 100755
--- a/utils/build/ssi/base/install_script_ssi_installer.sh
+++ b/utils/build/ssi/base/install_script_ssi_installer.sh
@@ -7,6 +7,8 @@ download_with_retry https://dd-agent.s3.amazonaws.com/scripts/install_script_age
 
 run_with_retry \
     "Datadog Agent installer" \
+    3 \
+    5 \
     env \
     DD_INSTALL_ONLY=true \
     DD_INSTALLER=true \

From d012eebbfbe7f2eb5529b93e058f285aee45a821 Mon Sep 17 00:00:00 2001
From: datadog-bits <263423550+datadog-bits@users.noreply.github.com>
Date: Mon, 14 Sep 2026 13:30:36 +0000
Subject: [PATCH 3/3] APMSP-3973 Make installer failure explicit

Co-authored-by: nccatoni <222672590+nccatoni@users.noreply.github.com>
---
 utils/build/ssi/base/install_script_ssi.sh           | 7 +++++--
 utils/build/ssi/base/install_script_ssi_installer.sh | 7 +++++--
 2 files changed, 10 insertions(+), 4 deletions(-)

diff --git a/utils/build/ssi/base/install_script_ssi.sh b/utils/build/ssi/base/install_script_ssi.sh
index 5f1ba9f4864..71f239d0526 100755
--- a/utils/build/ssi/base/install_script_ssi.sh
+++ b/utils/build/ssi/base/install_script_ssi.sh
@@ -54,7 +54,7 @@ if [ ! -s "install_script_agent7.sh" ]; then
     exit 1
 fi
 
-run_with_retry \
+if ! run_with_retry \
     "Datadog Agent installer" \
     3 \
     5 \
@@ -62,7 +62,10 @@ run_with_retry \
     "DD_REPO_URL=${DD_injection_repo_url}" \
     DD_INSTALL_ONLY=true \
     DD_APM_INSTRUMENTATION_ENABLED=host \
-    bash ./install_script_agent7.sh || exit 1
+    bash ./install_script_agent7.sh; then
+    echo "[ERROR] aborting SSI install after Datadog Agent installer failure" >&2
+    exit 1
+fi
 
 if [ -f /etc/debian_version ] || [ "$DISTRIBUTION" == "Debian" ] || [ "$DISTRIBUTION" == "Ubuntu" ]; then
     OS="Debian"
diff --git a/utils/build/ssi/base/install_script_ssi_installer.sh b/utils/build/ssi/base/install_script_ssi_installer.sh
index 3d823f72150..9a2abe30633 100755
--- a/utils/build/ssi/base/install_script_ssi_installer.sh
+++ b/utils/build/ssi/base/install_script_ssi_installer.sh
@@ -5,11 +5,14 @@ source ./download_with_retry.sh
 
 download_with_retry https://dd-agent.s3.amazonaws.com/scripts/install_script_agent7.sh || exit 1
 
-run_with_retry \
+if ! run_with_retry \
     "Datadog Agent installer" \
     3 \
     5 \
     env \
     DD_INSTALL_ONLY=true \
     DD_INSTALLER=true \
-    bash ./install_script_agent7.sh || exit 1
+    bash ./install_script_agent7.sh; then
+    echo "[ERROR] aborting SSI install after Datadog Agent installer failure" >&2
+    exit 1
+fi