diff --git a/cmd/root.go b/cmd/root.go
index a0b43cd..8658088 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -1,6 +1,7 @@
 package cmd
 
 import (
+	"context"
 	"crypto/tls"
 	"errors"
 	"fmt"
@@ -206,7 +207,17 @@ func rootCmdRun(cmd *cobra.Command, _ []string) {
 				st = state
 			}
 
-			r, err := s.Environment.IsRunning()
+			// Use a timed context here to avoid booting issues where Docker hangs for a
+			// specific container that would cause Wings to be un-bootable until the entire
+			// machine is rebooted. It is much better for us to just have a single failed
+			// server instance than an entire offline node.
+			//
+			// @see https://github.com/pterodactyl/panel/issues/2475
+			// @see https://github.com/pterodactyl/panel/issues/3358
+			ctx, cancel := context.WithTimeout(cmd.Context(), time.Second * 30)
+			defer cancel()
+
+			r, err := s.Environment.IsRunning(ctx)
 			// We ignore missing containers because we don't want to actually block booting of wings at this
 			// point. If we didn't do this, and you pruned all the images and then started wings you could
 			// end up waiting a long period of time for all the images to be re-pulled on Wings boot rather
@@ -235,7 +246,7 @@ func rootCmdRun(cmd *cobra.Command, _ []string) {
 				s.Log().Info("detected server is running, re-attaching to process...")
 
 				s.Environment.SetState(environment.ProcessRunningState)
-				if err := s.Environment.Attach(); err != nil {
+				if err := s.Environment.Attach(ctx); err != nil {
 					s.Log().WithField("error", err).Warn("failed to attach to running server environment")
 				}
 			} else {
diff --git a/environment/docker/container.go b/environment/docker/container.go
index 5ae066b..32d6df1 100644
--- a/environment/docker/container.go
+++ b/environment/docker/container.go
@@ -45,7 +45,7 @@ func (nw noopWriter) Write(b []byte) (int, error) {
 // Calling this function will poll resources for the container in the background
 // until the provided context is canceled by the caller. Failure to cancel said
 // context will cause background memory leaks as the goroutine will not exit.
-func (e *Environment) Attach() error {
+func (e *Environment) Attach(ctx context.Context) error {
 	if e.IsAttached() {
 		return nil
 	}
@@ -62,14 +62,17 @@ func (e *Environment) Attach() error {
 	}
 
 	// Set the stream again with the container.
-	if st, err := e.client.ContainerAttach(context.Background(), e.Id, opts); err != nil {
+	if st, err := e.client.ContainerAttach(ctx, e.Id, opts); err != nil {
 		return err
 	} else {
 		e.SetStream(&st)
 	}
 
 	go func() {
-		ctx, cancel := context.WithCancel(context.Background())
+		// Don't use the context provided to the function, that'll cause the polling to
+		// exit unexpectedly. We want a custom context for this, the one passed to the
+		// function is to avoid a hang situation when trying to attach to a container.
+		pollCtx, cancel := context.WithCancel(context.Background())
 		defer cancel()
 		defer e.stream.Close()
 		defer func() {
@@ -78,7 +81,7 @@ func (e *Environment) Attach() error {
 		}()
 
 		go func() {
-			if err := e.pollResources(ctx); err != nil {
+			if err := e.pollResources(pollCtx); err != nil {
 				if !errors.Is(err, context.Canceled) {
 					e.log().WithField("error", err).Error("error during environment resource polling")
 				} else {
diff --git a/environment/docker/environment.go b/environment/docker/environment.go
index c52df82..cacf6f7 100644
--- a/environment/docker/environment.go
+++ b/environment/docker/environment.go
@@ -128,20 +128,20 @@ func (e *Environment) Exists() (bool, error) {
 	return true, nil
 }
 
-// Determines if the server's docker container is currently running. If there is no container
-// present, an error will be raised (since this shouldn't be a case that ever happens under
-// correctly developed circumstances).
+// IsRunning determines if the server's docker container is currently running.
+// If there is no container present, an error will be raised (since this
+// shouldn't be a case that ever happens under correctly developed
+// circumstances).
 //
-// You can confirm if the instance wasn't found by using client.IsErrNotFound from the Docker
-// API.
+// You can confirm if the instance wasn't found by using client.IsErrNotFound
+// from the Docker API.
 //
 // @see docker/client/errors.go
-func (e *Environment) IsRunning() (bool, error) {
-	c, err := e.client.ContainerInspect(context.Background(), e.Id)
+func (e *Environment) IsRunning(ctx context.Context) (bool, error) {
+	c, err := e.client.ContainerInspect(ctx, e.Id)
 	if err != nil {
 		return false, err
 	}
-
 	return c.State.Running, nil
 }
 
diff --git a/environment/docker/power.go b/environment/docker/power.go
index f5eda4c..756edc7 100644
--- a/environment/docker/power.go
+++ b/environment/docker/power.go
@@ -17,16 +17,17 @@ import (
 	"github.com/pterodactyl/wings/remote"
 )
 
-// Run before the container starts and get the process configuration from the Panel.
-// This is important since we use this to check configuration files as well as ensure
-// we always have the latest version of an egg available for server processes.
+// OnBeforeStart run before the container starts and get the process
+// configuration from the Panel. This is important since we use this to check
+// configuration files as well as ensure we always have the latest version of
+// an egg available for server processes.
 //
-// This process will also confirm that the server environment exists and is in a bootable
-// state. This ensures that unexpected container deletion while Wings is running does
-// not result in the server becoming un-bootable.
-func (e *Environment) OnBeforeStart() error {
+// This process will also confirm that the server environment exists and is in
+// a bootable state. This ensures that unexpected container deletion while Wings
+// is running does not result in the server becoming un-bootable.
+func (e *Environment) OnBeforeStart(ctx context.Context) error {
 	// Always destroy and re-create the server container to ensure that synced data from the Panel is used.
-	if err := e.client.ContainerRemove(context.Background(), e.Id, types.ContainerRemoveOptions{RemoveVolumes: true}); err != nil {
+	if err := e.client.ContainerRemove(ctx, e.Id, types.ContainerRemoveOptions{RemoveVolumes: true}); err != nil {
 		if !client.IsErrNotFound(err) {
 			return errors.WrapIf(err, "environment/docker: failed to remove container during pre-boot")
 		}
@@ -46,10 +47,10 @@ func (e *Environment) OnBeforeStart() error {
 	return nil
 }
 
-// Starts the server environment and begins piping output to the event listeners for the
-// console. If a container does not exist, or needs to be rebuilt that will happen in the
-// call to OnBeforeStart().
-func (e *Environment) Start() error {
+// Start will start the server environment and begins piping output to the event
+// listeners for the console. If a container does not exist, or needs to be
+// rebuilt that will happen in the call to OnBeforeStart().
+func (e *Environment) Start(ctx context.Context) error {
 	sawError := false
 
 	// If sawError is set to true there was an error somewhere in the pipeline that
@@ -65,7 +66,7 @@ func (e *Environment) Start() error {
 		}
 	}()
 
-	if c, err := e.client.ContainerInspect(context.Background(), e.Id); err != nil {
+	if c, err := e.client.ContainerInspect(ctx, e.Id); err != nil {
 		// Do nothing if the container is not found, we just don't want to continue
 		// to the next block of code here. This check was inlined here to guard against
 		// a nil-pointer when checking c.State below.
@@ -79,7 +80,7 @@ func (e *Environment) Start() error {
 		if c.State.Running {
 			e.SetState(environment.ProcessRunningState)
 
-			return e.Attach()
+			return e.Attach(ctx)
 		}
 
 		// Truncate the log file, so we don't end up outputting a bunch of useless log information
@@ -101,21 +102,23 @@ func (e *Environment) Start() error {
 	// Run the before start function and wait for it to finish. This will validate that the container
 	// exists on the system, and rebuild the container if that is required for server booting to
 	// occur.
-	if err := e.OnBeforeStart(); err != nil {
+	if err := e.OnBeforeStart(ctx); err != nil {
 		return errors.WithStackIf(err)
 	}
 
-	ctx, cancel := context.WithTimeout(context.Background(), time.Second*10)
+	// If we cannot start & attach to the container in 30 seconds something has gone
+	// quite sideways and we should stop trying to avoid a hanging situation.
+	actx, cancel := context.WithTimeout(ctx, time.Second*30)
 	defer cancel()
 
-	if err := e.client.ContainerStart(ctx, e.Id, types.ContainerStartOptions{}); err != nil {
+	if err := e.client.ContainerStart(actx, e.Id, types.ContainerStartOptions{}); err != nil {
 		return errors.WrapIf(err, "environment/docker: failed to start container")
 	}
 
 	// No errors, good to continue through.
 	sawError = false
 
-	return e.Attach()
+	return e.Attach(actx)
 }
 
 // Stop stops the container that the server is running in. This will allow up to
diff --git a/environment/environment.go b/environment/environment.go
index c880161..f9568a2 100644
--- a/environment/environment.go
+++ b/environment/environment.go
@@ -1,6 +1,7 @@
 package environment
 
 import (
+	"context"
 	"os"
 
 	"github.com/pterodactyl/wings/events"
@@ -41,9 +42,9 @@ type ProcessEnvironment interface {
 	// a basic CLI environment this can probably just return true right away.
 	Exists() (bool, error)
 
-	// Determines if the environment is currently active and running a server process
-	// for this specific server instance.
-	IsRunning() (bool, error)
+	// IsRunning determines if the environment is currently active and running
+	// a server process for this specific server instance.
+	IsRunning(ctx context.Context) (bool, error)
 
 	// Performs an update of server resource limits without actually stopping the server
 	// process. This only executes if the environment supports it, otherwise it is
@@ -52,11 +53,11 @@ type ProcessEnvironment interface {
 
 	// Runs before the environment is started. If an error is returned starting will
 	// not occur, otherwise proceeds as normal.
-	OnBeforeStart() error
+	OnBeforeStart(ctx context.Context) error
 
 	// Starts a server instance. If the server instance is not in a state where it
 	// can be started an error should be returned.
-	Start() error
+	Start(ctx context.Context) error
 
 	// Stops a server instance. If the server is already stopped an error should
 	// not be returned.
@@ -84,10 +85,10 @@ type ProcessEnvironment interface {
 	// server.
 	Create() error
 
-	// Attaches to the server console environment and allows piping the output to a
-	// websocket or other internal tool to monitor output. Also allows you to later
+	// Attach attaches to the server console environment and allows piping the output
+	// to a websocket or other internal tool to monitor output. Also allows you to later
 	// send data into the environment's stdin.
-	Attach() error
+	Attach(ctx context.Context) error
 
 	// Sends the provided command to the running server instance.
 	SendCommand(string) error
diff --git a/router/router_server.go b/router/router_server.go
index 1125e78..31c93b7 100644
--- a/router/router_server.go
+++ b/router/router_server.go
@@ -101,7 +101,7 @@ func postServerPower(c *gin.Context) {
 func postServerCommands(c *gin.Context) {
 	s := ExtractServer(c)
 
-	if running, err := s.Environment.IsRunning(); err != nil {
+	if running, err := s.Environment.IsRunning(c.Request.Context()); err != nil {
 		NewServerError(err, s).Abort(c)
 		return
 	} else if !running {
diff --git a/router/websocket/websocket.go b/router/websocket/websocket.go
index d5f6d02..ff5855b 100644
--- a/router/websocket/websocket.go
+++ b/router/websocket/websocket.go
@@ -368,7 +368,9 @@ func (h *Handler) HandleInbound(m Message) error {
 		}
 	case SendServerLogsEvent:
 		{
-			if running, _ := h.server.Environment.IsRunning(); !running {
+			ctx, cancel := context.WithTimeout(context.Background(), time.Second * 5)
+			defer cancel()
+			if running, _ := h.server.Environment.IsRunning(ctx); !running {
 				return nil
 			}
 
diff --git a/server/power.go b/server/power.go
index d2df1a1..0f83304 100644
--- a/server/power.go
+++ b/server/power.go
@@ -128,7 +128,7 @@ func (s *Server) HandlePowerAction(action PowerAction, waitSeconds ...int) error
 			return err
 		}
 
-		return s.Environment.Start()
+		return s.Environment.Start(s.Context())
 	case PowerActionStop:
 		// We're specifically waiting for the process to be stopped here, otherwise the lock is released
 		// too soon, and you can rack up all sorts of issues.
@@ -151,7 +151,7 @@ func (s *Server) HandlePowerAction(action PowerAction, waitSeconds ...int) error
 			return err
 		}
 
-		return s.Environment.Start()
+		return s.Environment.Start(s.Context())
 	case PowerActionTerminate:
 		return s.Environment.Terminate(os.Kill)
 	}