diff --git a/internal/nomad/api_querier.go b/internal/nomad/api_querier.go
index fdf9356..3e487ab 100644
--- a/internal/nomad/api_querier.go
+++ b/internal/nomad/api_querier.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"github.com/getsentry/sentry-go"
 	"github.com/gorilla/websocket"
 	nomadApi "github.com/hashicorp/nomad/api"
 	"github.com/openHPI/poseidon/internal/config"
@@ -112,13 +113,18 @@ func (nc *nomadAPIClient) Execute(runnerID string,
 	}
 
 	var exitCode int
-	logging.StartSpan("nomad.execute.exec", "Execute Command in Allocation", ctx, func(ctx context.Context) {
-		debugWriter := NewSentryDebugWriter(stdout, ctx)
-		commands := []string{"/bin/bash", "-c", cmd}
-		exitCode, err = nc.client.Allocations().
-			Exec(ctx, allocation, TaskName, tty, commands, stdin, debugWriter, stderr, nil, nil)
-		debugWriter.Close(exitCode)
-	})
+	span := sentry.StartSpan(ctx, "nomad.execute.exec")
+	span.Description = "Execute Command in Allocation"
+
+	debugWriter := NewSentryDebugWriter(stdout, span.Context())
+	commands := []string{"/bin/bash", "-c", cmd}
+	exitCode, err = nc.client.Allocations().
+		Exec(span.Context(), allocation, TaskName, tty, commands, stdin, debugWriter, stderr, nil, nil)
+	debugWriter.Close(exitCode)
+
+	span.SetData("command", cmd)
+	span.Finish()
+
 	switch {
 	case err == nil:
 		return exitCode, nil
diff --git a/internal/nomad/nomad.go b/internal/nomad/nomad.go
index 38eb2d9..61580a1 100644
--- a/internal/nomad/nomad.go
+++ b/internal/nomad/nomad.go
@@ -474,7 +474,8 @@ const (
 )
 
 func prepareCommandWithoutTTY(command string, privilegedExecution bool) string {
-	command = setInnerDebugMessages(command, false)
+	const commandFieldAfterEnv = 4 // instead of "env CODEOCEAN=true /bin/bash -c sleep infinity" just "sleep infinity".
+	command = setInnerDebugMessages(command, commandFieldAfterEnv, -1)
 
 	command = setUserCommand(command, privilegedExecution)
 	command = unsetEnvironmentVariables(command)
@@ -482,7 +483,8 @@ func prepareCommandWithoutTTY(command string, privilegedExecution bool) string {
 }
 
 func prepareCommandTTY(command string, currentNanoTime int64, privilegedExecution bool) string {
-	command = setInnerDebugMessages(command, false)
+	const commandFieldAfterSettingEnvVariables = 4
+	command = setInnerDebugMessages(command, commandFieldAfterSettingEnvVariables, -1)
 
 	// Take the command to be executed and wrap it to redirect stderr.
 	stderrFifoPath := stderrFifo(currentNanoTime)
@@ -496,7 +498,7 @@ func prepareCommandTTY(command string, currentNanoTime int64, privilegedExecutio
 func prepareCommandTTYStdErr(currentNanoTime int64, privilegedExecution bool) string {
 	stderrFifoPath := stderrFifo(currentNanoTime)
 	command := fmt.Sprintf(stderrFifoCommandFormat, stderrFifoPath, stderrFifoPath, stderrFifoPath)
-	command = setInnerDebugMessages(command, false)
+	command = setInnerDebugMessages(command, 0, 1)
 	command = setUserCommand(command, privilegedExecution)
 	return command
 }
@@ -510,7 +512,8 @@ func unsetEnvironmentVariables(command string) string {
 	command = fmt.Sprintf(unsetEnvironmentVariablesFormat, unsetEnvironmentVariablesShell, command)
 
 	// Debug Message
-	command = fmt.Sprintf(timeDebugMessageFormatStart, "UnsetEnv", command)
+	const commandFieldBeforeBash = 2 // e.g. instead of "unset ${!NOMAD_@} && /bin/bash -c [...]" just "unset ${!NOMAD_@}".
+	command = injectStartDebugMessage(command, 0, commandFieldBeforeBash)
 	return command
 }
 
@@ -524,18 +527,36 @@ func setUserCommand(command string, privilegedExecution bool) string {
 	}
 
 	// Debug Message
-	command = fmt.Sprintf(timeDebugMessageFormatStart, "SetUser", command)
+	const commandFieldBeforeBash = 2 // e.g. instead of "/sbin/setuser user /bin/bash -c [...]" just "/sbin/setuser user".
+	command = injectStartDebugMessage(command, 0, commandFieldBeforeBash)
 	return command
 }
 
+func injectStartDebugMessage(command string, start uint, end int) string {
+	commandFields := strings.Fields(command)
+	if start < uint(len(commandFields)) {
+		commandFields = commandFields[start:]
+		end -= int(start)
+	}
+	if end >= 0 && end < len(commandFields) {
+		commandFields = commandFields[:end]
+	}
+
+	description := strings.Join(commandFields, " ")
+	if strings.HasPrefix(description, "\"") && strings.HasSuffix(description, "\"") {
+		description = description[1 : len(description)-1]
+	}
+
+	description = dto.BashEscapeCommand(description)
+	description = description[1 : len(description)-1] // The most outer quotes are not escaped!
+	return fmt.Sprintf(timeDebugMessageFormatStart, description, command)
+}
+
 // setInnerDebugMessages injects debug commands into the bash command.
 // The debug messages are parsed by the SentryDebugWriter.
-func setInnerDebugMessages(command string, includeCommandInDescription bool) (result string) {
-	description := "innerCommand"
-	if includeCommandInDescription {
-		description += fmt.Sprintf(" %s", command)
-	}
-	result = fmt.Sprintf(timeDebugMessageFormatStart, description, command)
+func setInnerDebugMessages(command string, descriptionStart uint, descriptionEnd int) (result string) {
+	result = injectStartDebugMessage(command, descriptionStart, descriptionEnd)
+
 	result = strings.TrimSuffix(result, ";")
-	return fmt.Sprintf(timeDebugMessageFormatEnd, result, "End")
+	return fmt.Sprintf(timeDebugMessageFormatEnd, result, "exit $ec")
 }
diff --git a/internal/nomad/sentry_debug_writer.go b/internal/nomad/sentry_debug_writer.go
index cc262b6..06d4308 100644
--- a/internal/nomad/sentry_debug_writer.go
+++ b/internal/nomad/sentry_debug_writer.go
@@ -34,6 +34,7 @@ type SentryDebugWriter struct {
 
 func NewSentryDebugWriter(target io.Writer, ctx context.Context) *SentryDebugWriter {
 	span := sentry.StartSpan(ctx, "nomad.execute.connect")
+	span.Description = "/bin/bash -c"
 	return &SentryDebugWriter{
 		Target:   target,
 		Ctx:      ctx,
diff --git a/pkg/dto/dto.go b/pkg/dto/dto.go
index 0854e17..553cb5c 100644
--- a/pkg/dto/dto.go
+++ b/pkg/dto/dto.go
@@ -41,17 +41,22 @@ func (er *ExecutionRequest) FullCommand() string {
 	return command
 }
 
-// WrapBashCommand escapes the passed command and wraps it into a new bash command.
+// BashEscapeCommand escapes the passed command and surrounds it with double-quotes.
 // The escaping includes the characters ", \, $, ` (comma-separated) as they are the exceptional characters
 // that still have a special meaning with double quotes. See the Bash Manual - Chapter Quoting.
 // We only handle the dollar-character and the backquote because the %q format already escapes the other two.
-func WrapBashCommand(command string) string {
-	command = fmt.Sprintf("/bin/bash -c %q", command)
+func BashEscapeCommand(command string) string {
+	command = fmt.Sprintf("%q", command)
 	command = strings.ReplaceAll(command, "$", "\\$")
 	command = strings.ReplaceAll(command, "`", "\\`")
 	return command
 }
 
+// WrapBashCommand escapes the passed command and wraps it into a new bash command.
+func WrapBashCommand(command string) string {
+	return fmt.Sprintf("/bin/bash -c %s", BashEscapeCommand(command))
+}
+
 // EnvironmentID is an id of an environment.
 type EnvironmentID int