diff --git a/.drone.yml b/.drone.yml
index cc5c53ae72f01..54bdf11eba8b8 100644
--- a/.drone.yml
+++ b/.drone.yml
@@ -561,7 +561,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow release-mac-amd64.yaml -workflow-ref=${DRONE_BRANCH}
+    -tag-workflow -timeout 2h30m0s -workflow release-mac-amd64.yaml -workflow-ref=${DRONE_BRANCH}
     -input oss-teleport-repo=${DRONE_REPO} -input oss-teleport-ref=${DRONE_COMMIT}
     -input "build-packages=false" -input "release-artifacts=false" '
   environment:
@@ -1299,7 +1299,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow release-linux-arm64.yml -workflow-ref=${DRONE_BRANCH}
+    -tag-workflow -timeout 2h30m0s -workflow release-linux-arm64.yml -workflow-ref=${DRONE_BRANCH}
     -input oss-teleport-repo=${DRONE_REPO} -input oss-teleport-ref=${DRONE_COMMIT}
     -input "upload-artifacts=false" '
   environment:
@@ -4317,7 +4317,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow release-mac-amd64.yaml -workflow-ref=${DRONE_TAG}
+    -tag-workflow -timeout 2h30m0s -workflow release-mac-amd64.yaml -workflow-ref=${DRONE_TAG}
     -input oss-teleport-repo=${DRONE_REPO} -input oss-teleport-ref=${DRONE_TAG} -input
     "build-packages=true" -input "release-artifacts=true" '
   environment:
@@ -4600,7 +4600,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow release-linux-arm64.yml -workflow-ref=${DRONE_TAG}
+    -tag-workflow -timeout 2h30m0s -workflow release-linux-arm64.yml -workflow-ref=${DRONE_TAG}
     -input oss-teleport-repo=${DRONE_REPO} -input oss-teleport-ref=${DRONE_TAG} -input
     "upload-artifacts=true" '
   environment:
@@ -7153,7 +7153,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow promote-teleport-oci-distroless.yml -workflow-ref=${DRONE_TAG}
+    -tag-workflow -timeout 2h30m0s -workflow promote-teleport-oci-distroless.yml -workflow-ref=${DRONE_TAG}
     -input "release-source-tag=${DRONE_TAG}" '
   environment:
     GHA_APP_KEY:
@@ -7212,7 +7212,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow promote-teleport-kube-agent-updater-oci.yml
+    -tag-workflow -timeout 2h30m0s -workflow promote-teleport-kube-agent-updater-oci.yml
     -workflow-ref=${DRONE_TAG} -input "release-source-tag=${DRONE_TAG}" '
   environment:
     GHA_APP_KEY:
@@ -8564,7 +8564,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow release-teleport-oci-distroless.yml -workflow-ref=${DRONE_TAG}
+    -tag-workflow -timeout 2h30m0s -workflow release-teleport-oci-distroless.yml -workflow-ref=${DRONE_TAG}
     -input oss-teleport-repo=${DRONE_REPO} -input oss-teleport-ref=${DRONE_TAG} '
   environment:
     GHA_APP_KEY:
@@ -8622,7 +8622,7 @@ steps:
   commands:
   - cd "/go/src/github.com/gravitational/teleport/build.assets/tooling"
   - 'go run ./cmd/gh-trigger-workflow -owner ${DRONE_REPO_OWNER} -repo teleport.e
-    -tag-workflow -timeout 1h0m0s -workflow release-teleport-kube-agent-updater-oci.yml
+    -tag-workflow -timeout 2h30m0s -workflow release-teleport-kube-agent-updater-oci.yml
     -workflow-ref=${DRONE_TAG} -input oss-teleport-repo=${DRONE_REPO} -input oss-teleport-ref=${DRONE_TAG} '
   environment:
     GHA_APP_KEY:
@@ -17223,6 +17223,6 @@ image_pull_secrets:
 - DOCKERHUB_CREDENTIALS
 ---
 kind: signature
-hmac: c602ba5582ac6031f496a000b5b9ec25272c30fd0ecd880ab6163cf3fc916b1a
+hmac: a593cf4660a1b71f183f12770b48f7bba347b8c1fbc50d5d59f8870ce53eeed8
 
 ...
diff --git a/dronegen/mac_gha.go b/dronegen/mac_gha.go
index 2359c04a0d5d0..49fd12e0d5dca 100644
--- a/dronegen/mac_gha.go
+++ b/dronegen/mac_gha.go
@@ -33,7 +33,7 @@ func darwinTagPipelineGHA() pipeline {
 				name:              "release-mac-amd64.yaml",
 				srcRefVar:         "DRONE_TAG",
 				ref:               "${DRONE_TAG}",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				slackOnError:      true,
 				shouldTagWorkflow: true,
 				inputs: map[string]string{
@@ -61,7 +61,7 @@ func darwinPushPipelineGHA() pipeline {
 				name:              "release-mac-amd64.yaml",
 				srcRefVar:         "DRONE_COMMIT",
 				ref:               "${DRONE_BRANCH}",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				slackOnError:      true,
 				shouldTagWorkflow: true,
 				inputs: map[string]string{
diff --git a/dronegen/promote.go b/dronegen/promote.go
index d0a32984520a3..8540a04581d76 100644
--- a/dronegen/promote.go
+++ b/dronegen/promote.go
@@ -27,7 +27,7 @@ func promoteBuildPipelines() []pipeline {
 		workflows: []ghaWorkflow{
 			{
 				name:              "promote-teleport-oci-distroless.yml",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				ref:               "${DRONE_TAG}",
 				shouldTagWorkflow: true,
 				inputs: map[string]string{
@@ -47,7 +47,7 @@ func promoteBuildPipelines() []pipeline {
 		workflows: []ghaWorkflow{
 			{
 				name:              "promote-teleport-kube-agent-updater-oci.yml",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				ref:               "${DRONE_TAG}",
 				shouldTagWorkflow: true,
 				inputs: map[string]string{
diff --git a/dronegen/push.go b/dronegen/push.go
index 92d0b87c8e40d..7e0c935777c82 100644
--- a/dronegen/push.go
+++ b/dronegen/push.go
@@ -83,7 +83,7 @@ func pushPipelines() []pipeline {
 		workflows: []ghaWorkflow{
 			{
 				name:              "release-linux-arm64.yml",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				slackOnError:      true,
 				srcRefVar:         "DRONE_COMMIT",
 				ref:               "${DRONE_BRANCH}",
diff --git a/dronegen/tag.go b/dronegen/tag.go
index b5eeaf570ea8d..bed5568e00b33 100644
--- a/dronegen/tag.go
+++ b/dronegen/tag.go
@@ -199,7 +199,7 @@ func tagPipelines() []pipeline {
 				name:              "release-linux-arm64.yml",
 				srcRefVar:         "DRONE_TAG",
 				ref:               "${DRONE_TAG}",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				shouldTagWorkflow: true,
 				inputs:            map[string]string{"upload-artifacts": "true"},
 			},
@@ -220,7 +220,7 @@ func tagPipelines() []pipeline {
 				name:              "release-teleport-oci-distroless.yml",
 				srcRefVar:         "DRONE_TAG",
 				ref:               "${DRONE_TAG}",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				shouldTagWorkflow: true,
 			},
 		},
@@ -235,7 +235,7 @@ func tagPipelines() []pipeline {
 				name:              "release-teleport-kube-agent-updater-oci.yml",
 				srcRefVar:         "DRONE_TAG",
 				ref:               "${DRONE_TAG}",
-				timeout:           60 * time.Minute,
+				timeout:           150 * time.Minute,
 				shouldTagWorkflow: true,
 			},
 		},