diff --git a/.github/workflows/studio-inference-smoke.yml b/.github/workflows/studio-inference-smoke.yml
index ce0c6f6ba4..ce4bf46425 100644
--- a/.github/workflows/studio-inference-smoke.yml
+++ b/.github/workflows/studio-inference-smoke.yml
@@ -467,15 +467,18 @@ jobs:
                   },
               )
               # Shared CI runners stall sporadically, so retry transport-level
-              # failures only; HTTP status errors surface immediately.
-              for attempt in range(3):
+              # failures only; HTTP status errors surface immediately. Long
+              # probes (timeout > 300s) get a single attempt so the worst
+              # case stays inside the job's timeout-minutes budget.
+              attempts = 3 if timeout <= 300 else 1
+              for attempt in range(attempts):
                   try:
                       with urllib.request.urlopen(req, timeout = timeout) as resp:
                           return resp.status, json.loads(resp.read().decode())
                   except urllib.error.HTTPError:
                       raise
                   except (TimeoutError, ConnectionError, urllib.error.URLError) as exc:
-                      if attempt == 2:
+                      if attempt == attempts - 1:
                           raise
                       print(f"[retry] {path}: {exc!r}", flush = True)
                       time.sleep(15)
@@ -972,15 +975,18 @@ jobs:
                   },
               )
               # Shared CI runners stall sporadically, so retry transport-level
-              # failures only; HTTP status errors surface immediately.
-              for attempt in range(3):
+              # failures only; HTTP status errors surface immediately. Long
+              # probes (timeout > 300s) get a single attempt so the worst
+              # case stays inside the job's timeout-minutes budget.
+              attempts = 3 if timeout <= 300 else 1
+              for attempt in range(attempts):
                   try:
                       with urllib.request.urlopen(req, timeout = timeout) as resp:
                           return resp.status, json.loads(resp.read().decode())
                   except urllib.error.HTTPError:
                       raise
                   except (TimeoutError, ConnectionError, urllib.error.URLError) as exc:
-                      if attempt == 2:
+                      if attempt == attempts - 1:
                           raise
                       print(f"[retry] {path}: {exc!r}", flush = True)
                       time.sleep(15)
diff --git a/.github/workflows/studio-mac-inference-smoke.yml b/.github/workflows/studio-mac-inference-smoke.yml
index d9d98e3a16..805817b518 100644
--- a/.github/workflows/studio-mac-inference-smoke.yml
+++ b/.github/workflows/studio-mac-inference-smoke.yml
@@ -453,15 +453,18 @@ jobs:
                   },
               )
               # Shared CI runners stall sporadically, so retry transport-level
-              # failures only; HTTP status errors surface immediately.
-              for attempt in range(3):
+              # failures only; HTTP status errors surface immediately. Long
+              # probes (timeout > 300s) get a single attempt so the worst
+              # case stays inside the job's timeout-minutes budget.
+              attempts = 3 if timeout <= 300 else 1
+              for attempt in range(attempts):
                   try:
                       with urllib.request.urlopen(req, timeout = timeout) as resp:
                           return resp.status, json.loads(resp.read().decode())
                   except urllib.error.HTTPError:
                       raise
                   except (TimeoutError, ConnectionError, urllib.error.URLError) as exc:
-                      if attempt == 2:
+                      if attempt == attempts - 1:
                           raise
                       print(f"[retry] {path}: {exc!r}", flush = True)
                       time.sleep(15)
@@ -864,15 +867,18 @@ jobs:
                   },
               )
               # Shared CI runners stall sporadically, so retry transport-level
-              # failures only; HTTP status errors surface immediately.
-              for attempt in range(3):
+              # failures only; HTTP status errors surface immediately. Long
+              # probes (timeout > 300s) get a single attempt so the worst
+              # case stays inside the job's timeout-minutes budget.
+              attempts = 3 if timeout <= 300 else 1
+              for attempt in range(attempts):
                   try:
                       with urllib.request.urlopen(req, timeout = timeout) as resp:
                           return resp.status, json.loads(resp.read().decode())
                   except urllib.error.HTTPError:
                       raise
                   except (TimeoutError, ConnectionError, urllib.error.URLError) as exc:
-                      if attempt == 2:
+                      if attempt == attempts - 1:
                           raise
                       print(f"[retry] {path}: {exc!r}", flush = True)
                       time.sleep(15)
diff --git a/.github/workflows/studio-windows-inference-smoke.yml b/.github/workflows/studio-windows-inference-smoke.yml
index 00cf9adcf1..740cde15fb 100644
--- a/.github/workflows/studio-windows-inference-smoke.yml
+++ b/.github/workflows/studio-windows-inference-smoke.yml
@@ -659,15 +659,18 @@ jobs:
                   },
               )
               # Shared CI runners stall sporadically, so retry transport-level
-              # failures only; HTTP status errors surface immediately.
-              for attempt in range(3):
+              # failures only; HTTP status errors surface immediately. Long
+              # probes (timeout > 300s) get a single attempt so the worst
+              # case stays inside the job's timeout-minutes budget.
+              attempts = 3 if timeout <= 300 else 1
+              for attempt in range(attempts):
                   try:
                       with urllib.request.urlopen(req, timeout = timeout) as resp:
                           return resp.status, json.loads(resp.read().decode())
                   except urllib.error.HTTPError:
                       raise
                   except (TimeoutError, ConnectionError, urllib.error.URLError) as exc:
-                      if attempt == 2:
+                      if attempt == attempts - 1:
                           raise
                       print(f"[retry] {path}: {exc!r}", flush = True)
                       time.sleep(15)
@@ -1098,15 +1101,18 @@ jobs:
                   },
               )
               # Shared CI runners stall sporadically, so retry transport-level
-              # failures only; HTTP status errors surface immediately.
-              for attempt in range(3):
+              # failures only; HTTP status errors surface immediately. Long
+              # probes (timeout > 300s) get a single attempt so the worst
+              # case stays inside the job's timeout-minutes budget.
+              attempts = 3 if timeout <= 300 else 1
+              for attempt in range(attempts):
                   try:
                       with urllib.request.urlopen(req, timeout = timeout) as resp:
                           return resp.status, json.loads(resp.read().decode())
                   except urllib.error.HTTPError:
                       raise
                   except (TimeoutError, ConnectionError, urllib.error.URLError) as exc:
-                      if attempt == 2:
+                      if attempt == attempts - 1:
                           raise
                       print(f"[retry] {path}: {exc!r}", flush = True)
                       time.sleep(15)