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