diff --git a/internal/nomad/api_querier.go b/internal/nomad/api_querier.go
index 5e870cd..70f082b 100644
--- a/internal/nomad/api_querier.go
+++ b/internal/nomad/api_querier.go
@@ -89,6 +89,7 @@ func (nc *nomadAPIClient) Execute(runnerID string,
 	ctx context.Context, command []string, tty bool,
 	stdin io.Reader, stdout, stderr io.Writer,
 ) (int, error) {
+	log.WithField("command", command).Trace("Requesting Nomad Exec")
 	var allocations []*nomadApi.AllocationListStub
 	var err error
 	logging.StartSpan("nomad.execute.list", "List Allocations for id", ctx, func(_ context.Context) {
@@ -111,7 +112,10 @@ func (nc *nomadAPIClient) Execute(runnerID string,
 
 	var exitCode int
 	logging.StartSpan("nomad.execute.exec", "Execute Command in Allocation", ctx, func(ctx context.Context) {
-		exitCode, err = nc.client.Allocations().Exec(ctx, allocation, TaskName, tty, command, stdin, stdout, stderr, nil, nil)
+		debugWriter := NewSentryDebugWriter(stdout, ctx)
+		exitCode, err = nc.client.Allocations().
+			Exec(ctx, allocation, TaskName, tty, command, stdin, debugWriter, stderr, nil, nil)
+		debugWriter.Close(exitCode)
 	})
 	switch {
 	case err == nil:
diff --git a/internal/nomad/nomad.go b/internal/nomad/nomad.go
index 81d1d2e..06fef8d 100644
--- a/internal/nomad/nomad.go
+++ b/internal/nomad/nomad.go
@@ -398,8 +398,7 @@ func (a *APIClient) ExecuteCommand(jobID string,
 		return a.executeCommandInteractivelyWithStderr(jobID, ctx, command, privilegedExecution, stdin, stdout, stderr)
 	}
 	command = prepareCommandWithoutTTY(command, privilegedExecution)
-	debugWriter := &SentryDebugWriter{Target: stdout, Ctx: ctx}
-	exitCode, err := a.apiQuerier.Execute(jobID, ctx, command, tty, stdin, debugWriter, stderr)
+	exitCode, err := a.apiQuerier.Execute(jobID, ctx, command, tty, stdin, stdout, stderr)
 	if err != nil {
 		return 1, fmt.Errorf("error executing command in job %s: %w", jobID, err)
 	}
@@ -423,9 +422,8 @@ func (a *APIClient) executeCommandInteractivelyWithStderr(allocationID string, c
 
 		// Catch stderr in separate execution.
 		logging.StartSpan("nomad.execute.stderr", "Execution for separate StdErr", ctx, func(ctx context.Context) {
-			debugWriterStderr := &SentryDebugWriter{Target: stderr, Ctx: ctx}
 			exit, err := a.Execute(allocationID, ctx, prepareCommandTTYStdErr(currentNanoTime, privilegedExecution), true,
-				nullio.Reader{Ctx: readingContext}, debugWriterStderr, io.Discard)
+				nullio.Reader{Ctx: readingContext}, stderr, io.Discard)
 			if err != nil {
 				log.WithError(err).WithField("runner", allocationID).Warn("Stderr task finished with error")
 			}
@@ -437,8 +435,7 @@ func (a *APIClient) executeCommandInteractivelyWithStderr(allocationID string, c
 	var exit int
 	var err error
 	logging.StartSpan("nomad.execute.tty", "Interactive Execution", ctx, func(ctx context.Context) {
-		debugWriter := &SentryDebugWriter{Target: stdout, Ctx: ctx}
-		exit, err = a.Execute(allocationID, ctx, command, true, stdin, debugWriter, io.Discard)
+		exit, err = a.Execute(allocationID, ctx, command, true, stdin, stdout, io.Discard)
 	})
 
 	// Wait until the stderr catch command finished to make sure we receive all output.
@@ -481,7 +478,7 @@ func prepareCommandWithoutTTY(srcCommands []string, privilegedExecution bool) []
 	commands := make([]string, len(srcCommands)) // nozero The size is required for the copy.
 	copy(commands, srcCommands)
 
-	commands[len(commands)-1] = setInnerDebugMessages(commands[len(commands)-1])
+	commands[len(commands)-1] = setInnerDebugMessages(commands[len(commands)-1], false)
 	commands = setUserCommand(commands, privilegedExecution)
 	commands[len(commands)-1] = fmt.Sprintf("'%s'", commands[len(commands)-1])
 	cmd := strings.Join(commands, " ")
@@ -495,7 +492,7 @@ func prepareCommandTTY(srcCommands []string, currentNanoTime int64, privilegedEx
 	commands := make([]string, len(srcCommands)) // nozero The size is required for the copy.
 	copy(commands, srcCommands)
 
-	commands[len(commands)-1] = setInnerDebugMessages(commands[len(commands)-1])
+	commands[len(commands)-1] = setInnerDebugMessages(commands[len(commands)-1], true)
 	commands = setUserCommand(commands, privilegedExecution)
 	// Take the last command which is the one to be executed and wrap it to redirect stderr.
 	stderrFifoPath := stderrFifo(currentNanoTime)
@@ -511,7 +508,7 @@ func prepareCommandTTY(srcCommands []string, currentNanoTime int64, privilegedEx
 func prepareCommandTTYStdErr(currentNanoTime int64, privilegedExecution bool) []string {
 	stderrFifoPath := stderrFifo(currentNanoTime)
 	cmd := fmt.Sprintf(stderrFifoCommandFormat, stderrFifoPath, stderrFifoPath, stderrFifoPath)
-	cmd = setInnerDebugMessages(cmd)
+	cmd = setInnerDebugMessages(cmd, false)
 	return setUserCommand([]string{"bash", "-c", cmd}, privilegedExecution)
 }
 
@@ -529,8 +526,14 @@ func stderrFifo(id int64) string {
 	return fmt.Sprintf(stderrFifoFormat, id)
 }
 
-func setInnerDebugMessages(command string) (result string) {
-	result = fmt.Sprintf(timeDebugMessageFormatStart, "innerCommand", 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)
 	result = strings.TrimSuffix(result, ";")
 	return fmt.Sprintf(timeDebugMessageFormatEnd, result, "End")
 }
diff --git a/internal/nomad/sentry_debug_writer.go b/internal/nomad/sentry_debug_writer.go
index b8ff0b3..834d51c 100644
--- a/internal/nomad/sentry_debug_writer.go
+++ b/internal/nomad/sentry_debug_writer.go
@@ -17,13 +17,11 @@ const (
 	timeDebugMessageFormatStart = timeDebugMessageFormat + "; %s"
 	// Format Parameters: 1. command, 2. Debug Comment.
 	timeDebugMessageFormatEnd = "%s && " + timeDebugMessageFormat
-
-	timeDebugMessagePatternGroupText = 1
-	timeDebugMessagePatternGroupTime = 2
 )
 
 var (
-	timeDebugMessagePattern      = regexp.MustCompile(`\x1EPoseidon (?P<text>\w+) (?P<time>\d+)\x1E`)
+	timeDebugMessagePattern = regexp.
+				MustCompile(`(?P<before>.*)\x1EPoseidon (?P<text>.+) (?P<time>\d{13})\x1E(?P<after>.*)`)
 	timeDebugMessagePatternStart = regexp.MustCompile(`\x1EPoseidon`)
 )
 
@@ -36,54 +34,81 @@ type SentryDebugWriter struct {
 	lastSpan *sentry.Span
 }
 
-// Improve: Handling of a split debug messages (usually p is exactly one debug message, not less and not more).
+func NewSentryDebugWriter(target io.Writer, ctx context.Context) *SentryDebugWriter {
+	span := sentry.StartSpan(ctx, "nomad.execute.connect")
+	return &SentryDebugWriter{
+		Target:   target,
+		Ctx:      ctx,
+		lastSpan: span,
+	}
+}
+
+// Improve: Handling of a split debug messages (usually, p is exactly one debug message, not less and not more).
 func (s *SentryDebugWriter) Write(p []byte) (n int, err error) {
 	if !timeDebugMessagePatternStart.Match(p) {
 		count, err := s.Target.Write(p)
 		if err != nil {
-			err = fmt.Errorf("SentryDebugWriter Forwarded: %w", err)
+			err = fmt.Errorf("SentryDebugWriter Forwarded Error: %w", err)
 		}
 		return count, err
 	}
 
-	loc := timeDebugMessagePattern.FindIndex(p)
-	if loc == nil {
+	match := matchAndMapTimeDebugMessage(p)
+	if match == nil {
 		log.WithField("data", p).Warn("Exec debug message could not be read completely")
 		return 0, nil
 	}
 
-	go s.handleTimeDebugMessage(p[loc[0]:loc[1]])
+	go s.handleTimeDebugMessage(match)
 
-	debugMessageLength := loc[1] - loc[0]
-	if debugMessageLength < len(p) {
-		count, err := s.Write(append(p[0:loc[0]], p[loc[1]:]...))
-		return debugMessageLength + count, err
+	lengthRemainingData := len(match["before"]) + len(match["after"])
+	if lengthRemainingData > 0 {
+		count, err := s.Write(append(match["before"], match["after"]...))
+		return len(p) - (lengthRemainingData - count), err
 	} else {
-		return debugMessageLength, nil
+		return len(p), nil
 	}
 }
 
-func (s *SentryDebugWriter) handleTimeDebugMessage(message []byte) {
+func (s *SentryDebugWriter) Close(exitCode int) {
 	if s.lastSpan != nil {
+		s.lastSpan.Op = "nomad.execute.disconnect"
+		s.lastSpan.SetTag("exit_code", strconv.Itoa(exitCode))
+		s.lastSpan.Finish()
+	}
+}
+
+// handleTimeDebugMessage transforms one time debug message into a Sentry span.
+// It requires match to contain the keys `time` and `text`.
+func (s *SentryDebugWriter) handleTimeDebugMessage(match map[string][]byte) {
+	timestamp, err := strconv.ParseInt(string(match["time"]), 10, 64)
+	if err != nil {
+		log.WithField("match", match).Warn("Could not parse Unix timestamp")
+		return
+	}
+
+	if s.lastSpan != nil {
+		s.lastSpan.EndTime = time.UnixMilli(timestamp)
+		s.lastSpan.SetData("latency", time.Since(time.UnixMilli(timestamp)).String())
 		s.lastSpan.Finish()
 	}
 
-	matches := timeDebugMessagePattern.FindSubmatch(message)
-	if matches == nil {
-		log.WithField("msg", message).Error("Cannot parse passed time debug message")
-		return
-	}
-
-	timestamp, err := strconv.ParseInt(string(matches[timeDebugMessagePatternGroupTime]), 10, 64)
-	if err != nil {
-		log.WithField("matches", matches).Warn("Could not parse Unix timestamp")
-		return
-	}
-	s.lastSpan = sentry.StartSpan(s.Ctx, "nomad.execute.pipe")
-	s.lastSpan.Description = string(matches[timeDebugMessagePatternGroupText])
-	s.lastSpan.StartTime = time.UnixMilli(timestamp)
-	s.lastSpan.Finish()
-
 	s.lastSpan = sentry.StartSpan(s.Ctx, "nomad.execute.bash")
-	s.lastSpan.Description = string(matches[timeDebugMessagePatternGroupText])
+	s.lastSpan.Description = string(match["text"])
+	s.lastSpan.StartTime = time.UnixMilli(timestamp)
+}
+
+func matchAndMapTimeDebugMessage(p []byte) map[string][]byte {
+	match := timeDebugMessagePattern.FindSubmatch(p)
+	if match == nil {
+		return nil
+	}
+
+	labelMap := make(map[string][]byte)
+	for i, name := range timeDebugMessagePattern.SubexpNames() {
+		if i != 0 && name != "" {
+			labelMap[name] = match[i]
+		}
+	}
+	return labelMap
 }
diff --git a/internal/nomad/sentry_debug_writer_test.go b/internal/nomad/sentry_debug_writer_test.go
index 4b27fe1..090777a 100644
--- a/internal/nomad/sentry_debug_writer_test.go
+++ b/internal/nomad/sentry_debug_writer_test.go
@@ -2,6 +2,7 @@ package nomad
 
 import (
 	"bytes"
+	"context"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"testing"
@@ -9,7 +10,7 @@ import (
 
 func TestSentryDebugWriter_Write(t *testing.T) {
 	buf := &bytes.Buffer{}
-	w := SentryDebugWriter{Target: buf}
+	w := SentryDebugWriter{Target: buf, Ctx: context.Background()}
 
 	description := "TestDebugMessageDescription"
 	data := "\x1EPoseidon " + description + " 1676646791482\x1E"