diff --git a/assets/aws/files/system/teleport-acm.service b/assets/aws/files/system/teleport-acm.service
index 91d7e1a84fa5d..6dcab6c09d70b 100644
--- a/assets/aws/files/system/teleport-acm.service
+++ b/assets/aws/files/system/teleport-acm.service
@@ -11,6 +11,7 @@ Restart=always
 RestartSec=5
 RuntimeDirectory=teleport
 ExecStart=/usr/local/bin/teleport start --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport/teleport.pid"
 PIDFile=/run/teleport/teleport.pid
 LimitNOFILE=524288
diff --git a/assets/aws/files/system/teleport-auth.service b/assets/aws/files/system/teleport-auth.service
index f1b99b9879a0d..9cd5c39e05f89 100644
--- a/assets/aws/files/system/teleport-auth.service
+++ b/assets/aws/files/system/teleport-auth.service
@@ -11,7 +11,8 @@ Restart=always
 RestartSec=5
 RuntimeDirectory=teleport
 ExecStart=/usr/local/bin/teleport start --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport/teleport.pid"
 PIDFile=/run/teleport/teleport.pid
 LimitNOFILE=524288
 
diff --git a/assets/aws/files/system/teleport-node.service b/assets/aws/files/system/teleport-node.service
index b0b26651ac970..32107a77b7428 100644
--- a/assets/aws/files/system/teleport-node.service
+++ b/assets/aws/files/system/teleport-node.service
@@ -12,7 +12,8 @@ RestartSec=5
 RuntimeDirectory=teleport
 ExecStartPre=/usr/local/bin/teleport-ssm-get-token
 ExecStart=/usr/local/bin/teleport start --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport/teleport.pid"
 PIDFile=/run/teleport/teleport.pid
 LimitNOFILE=524288
 
diff --git a/assets/aws/files/system/teleport-proxy-acm.service b/assets/aws/files/system/teleport-proxy-acm.service
index e711afb8fc663..260b914841746 100644
--- a/assets/aws/files/system/teleport-proxy-acm.service
+++ b/assets/aws/files/system/teleport-proxy-acm.service
@@ -13,7 +13,8 @@ RuntimeDirectory=teleport
 EnvironmentFile=/etc/teleport.d/conf
 ExecStartPre=/usr/local/bin/teleport-ssm-get-token
 ExecStart=/usr/local/bin/teleport start --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport/teleport.pid"
 PIDFile=/run/teleport/teleport.pid
 LimitNOFILE=524288
 
diff --git a/assets/aws/files/system/teleport-proxy.service b/assets/aws/files/system/teleport-proxy.service
index 4d6f729bfc7d6..5f88872d07bbe 100644
--- a/assets/aws/files/system/teleport-proxy.service
+++ b/assets/aws/files/system/teleport-proxy.service
@@ -14,7 +14,8 @@ EnvironmentFile=/etc/teleport.d/conf
 ExecStartPre=/usr/local/bin/teleport-ssm-get-token
 ExecStartPre=/bin/aws s3 sync s3://${TELEPORT_S3_BUCKET}/live/${TELEPORT_DOMAIN_NAME} /var/lib/teleport
 ExecStart=/usr/local/bin/teleport start --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport/teleport.pid"
 PIDFile=/run/teleport/teleport.pid
 LimitNOFILE=524288
 
diff --git a/assets/aws/files/system/teleport.service b/assets/aws/files/system/teleport.service
index 5e6a091f75d47..73e7fce096891 100644
--- a/assets/aws/files/system/teleport.service
+++ b/assets/aws/files/system/teleport.service
@@ -12,7 +12,8 @@ RestartSec=5
 RuntimeDirectory=teleport
 ExecStartPre=/usr/local/bin/teleport-all-pre-start
 ExecStart=/usr/local/bin/teleport start --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport/teleport.pid"
 PIDFile=/run/teleport/teleport.pid
 LimitNOFILE=524288
 
diff --git a/examples/systemd/fips/teleport.service b/examples/systemd/fips/teleport.service
index a87df21500486..7a0cb36770421 100644
--- a/examples/systemd/fips/teleport.service
+++ b/examples/systemd/fips/teleport.service
@@ -7,7 +7,8 @@ Type=simple
 Restart=on-failure
 EnvironmentFile=-/etc/default/teleport
 ExecStart=/usr/local/bin/teleport start --config /etc/teleport.yaml --fips --pid-file=/run/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport.pid"
 PIDFile=/run/teleport.pid
 LimitNOFILE=524288
 
diff --git a/examples/systemd/production/auth/teleport.service b/examples/systemd/production/auth/teleport.service
index 51309784e2372..94e5a7887a122 100644
--- a/examples/systemd/production/auth/teleport.service
+++ b/examples/systemd/production/auth/teleport.service
@@ -11,7 +11,8 @@ Restart=on-failure
 # --roles='proxy,auth,node' is the default value
 # if none is set
 ExecStart=/usr/local/bin/teleport start --roles=auth --config=/etc/teleport.yaml --diag-addr=127.0.0.1:3000 --pid-file=/run/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport.pid"
 PIDFile=/run/teleport.pid
 LimitNOFILE=524288
 
diff --git a/examples/systemd/production/node/teleport.service b/examples/systemd/production/node/teleport.service
index 0845c6c05ec8d..82f1ebc26f12c 100644
--- a/examples/systemd/production/node/teleport.service
+++ b/examples/systemd/production/node/teleport.service
@@ -11,7 +11,8 @@ Restart=on-failure
 # --roles='proxy,auth,node' is the default value
 # if none is set
 ExecStart=/usr/local/bin/teleport start --roles=node --config=/etc/teleport.yaml --pid-file=/run/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport.pid"
 PIDFile=/run/teleport.pid
 LimitNOFILE=524288
 
diff --git a/examples/systemd/production/proxy/teleport.service b/examples/systemd/production/proxy/teleport.service
index 029785694a49e..2a0a191d513f2 100644
--- a/examples/systemd/production/proxy/teleport.service
+++ b/examples/systemd/production/proxy/teleport.service
@@ -11,7 +11,8 @@ Restart=on-failure
 # --roles='proxy,auth,node' is the default value
 # if none is set
 ExecStart=/usr/local/bin/teleport start --roles=proxy --config=/etc/teleport.yaml --pid-file=/run/teleport.pid
-ExecReload=pkill -HUP -L -F /run/teleport.pid
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport.pid"
 PIDFile=/run/teleport.pid
 LimitNOFILE=524288
 
diff --git a/examples/systemd/teleport.service b/examples/systemd/teleport.service
index b5d71b1e1de31..d641fb2f13287 100644
--- a/examples/systemd/teleport.service
+++ b/examples/systemd/teleport.service
@@ -7,6 +7,7 @@ Type=simple
 Restart=on-failure
 EnvironmentFile=-/etc/default/teleport
 ExecStart=/usr/local/bin/teleport start --config /etc/teleport.yaml --pid-file=/run/teleport.pid
+# systemd before 239 needs an absolute path
 ExecReload=/bin/sh -c "exec pkill -HUP -L -F /run/teleport.pid"
 PIDFile=/run/teleport.pid
 LimitNOFILE=524288
diff --git a/lib/config/systemd.go b/lib/config/systemd.go
index 6146b89926752..5992b119c2cb5 100644
--- a/lib/config/systemd.go
+++ b/lib/config/systemd.go
@@ -47,7 +47,8 @@ Type=simple
 Restart=on-failure
 EnvironmentFile=-{{ .EnvironmentFile }}
 ExecStart={{ .TeleportInstallationFile }} start --config {{ .TeleportConfigPath }} --pid-file={{ .PIDFile }}
-ExecReload=pkill -HUP -L -F "{{ .PIDFile }}"
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F {{ .PIDFile }}"
 PIDFile={{ .PIDFile }}
 LimitNOFILE={{ .FileDescriptorLimit }}
 
diff --git a/lib/config/testdata/TestWriteSystemdUnitFile.golden b/lib/config/testdata/TestWriteSystemdUnitFile.golden
index 8153d3270b129..b852e9399ee28 100644
--- a/lib/config/testdata/TestWriteSystemdUnitFile.golden
+++ b/lib/config/testdata/TestWriteSystemdUnitFile.golden
@@ -7,7 +7,8 @@ Type=simple
 Restart=on-failure
 EnvironmentFile=-/custom/env/dir/teleport
 ExecStart=/custom/install/dir/teleport start --config /etc/teleport.yaml --pid-file=/custom/pid/dir/teleport.pid
-ExecReload=pkill -HUP -L -F "/custom/pid/dir/teleport.pid"
+# systemd before 239 needs an absolute path
+ExecReload=/bin/sh -c "exec pkill -HUP -L -F /custom/pid/dir/teleport.pid"
 PIDFile=/custom/pid/dir/teleport.pid
 LimitNOFILE=16384