From 8222d44c55ceb1b7166149b52bcd1f6a6956ada9 Mon Sep 17 00:00:00 2001
From: Benjamin Rewis <32186188+benjirewis@users.noreply.github.com>
Date: Fri, 17 Jan 2025 14:12:56 -0500
Subject: [PATCH] Further bump timeouts when behind SOCKS proxy (#4725)

---
 config/reader.go          |  2 +-
 internal/cloud/service.go | 26 ++++++++++++++++++++++----
 logging/net_appender.go   |  2 +-
 3 files changed, 24 insertions(+), 6 deletions(-)

diff --git a/config/reader.go b/config/reader.go
index 629df091a5e..1898e41bd6d 100644
--- a/config/reader.go
+++ b/config/reader.go
@@ -35,7 +35,7 @@ var (
 const (
 	initialReadTimeout     = 1 * time.Second
 	readTimeout            = 5 * time.Second
-	readTimeoutBehindProxy = 15 * time.Second
+	readTimeoutBehindProxy = time.Minute
 	// PackagesDirName is where packages go underneath viamDotDir.
 	PackagesDirName = "packages"
 	// LocalPackagesSuffix is used by the local package manager.
diff --git a/internal/cloud/service.go b/internal/cloud/service.go
index f4fe4d4731b..5cad0f8a06c 100644
--- a/internal/cloud/service.go
+++ b/internal/cloud/service.go
@@ -5,6 +5,7 @@ package cloud
 import (
 	"context"
 	"errors"
+	"os"
 	"sync"
 	"time"
 
@@ -16,8 +17,13 @@ import (
 	"go.viam.com/rdk/resource"
 )
 
-// SubtypeName is a constant that identifies the internal cloud connection resource subtype string.
-const SubtypeName = "cloud_connection"
+const (
+	// SubtypeName is a constant that identifies the internal cloud connection resource
+	// subtype string.
+	SubtypeName               = "cloud_connection"
+	connectTimeout            = 5 * time.Second
+	connectTimeoutBehindProxy = time.Minute
+)
 
 // API is the fully qualified API for the internal cloud connection service.
 var API = resource.APINamespaceRDKInternal.WithServiceType(SubtypeName)
@@ -74,7 +80,13 @@ func (cm *cloudManagedService) AcquireConnection(ctx context.Context) (string, r
 	}
 
 	ctx = rpc.ContextWithDialer(ctx, cm.dialer)
-	timeOutCtx, cancel := context.WithTimeout(ctx, 5*time.Second)
+	timeout := connectTimeout
+	// When environment indicates we are behind a proxy, bump timeout. Network
+	// operations tend to take longer when behind a proxy.
+	if os.Getenv(rpc.SocksProxyEnvVar) != "" {
+		timeout = connectTimeoutBehindProxy
+	}
+	timeOutCtx, cancel := context.WithTimeout(ctx, timeout)
 	defer cancel()
 	conn, err := config.CreateNewGRPCClient(timeOutCtx, &cm.cloudCfg, cm.logger)
 	return cm.cloudCfg.ID, conn, err
@@ -93,7 +105,13 @@ func (cm *cloudManagedService) AcquireConnectionAPIKey(ctx context.Context,
 	}
 
 	ctx = rpc.ContextWithDialer(ctx, cm.dialer)
-	timeOutCtx, cancel := context.WithTimeout(ctx, 5*time.Second)
+	timeout := connectTimeout
+	// When environment indicates we are behind a proxy, bump timeout. Network
+	// operations tend to take longer when behind a proxy.
+	if os.Getenv(rpc.SocksProxyEnvVar) != "" {
+		timeout = connectTimeoutBehindProxy
+	}
+	timeOutCtx, cancel := context.WithTimeout(ctx, timeout)
 	defer cancel()
 	conn, err := config.CreateNewGRPCClientWithAPIKey(timeOutCtx, &cm.cloudCfg, apiKey, apiKeyID, cm.logger)
 	return cm.cloudCfg.ID, conn, err
diff --git a/logging/net_appender.go b/logging/net_appender.go
index b14176f629e..b62179544e3 100644
--- a/logging/net_appender.go
+++ b/logging/net_appender.go
@@ -24,7 +24,7 @@ var (
 	writeBatchSize             = 100
 	errUninitializedConnection = errors.New("sharedConn is true and connection is not initialized")
 	logWriteTimeout            = 4 * time.Second
-	logWriteTimeoutBehindProxy = 12 * time.Second
+	logWriteTimeoutBehindProxy = time.Minute
 )
 
 // CloudConfig contains the necessary inputs to send logs to the app backend over grpc.