diff --git a/main/cmds.go b/main/cmds.go
index 65c37b5..d5e2bba 100644
--- a/main/cmds.go
+++ b/main/cmds.go
@@ -116,7 +116,7 @@ func uninstall(ctx *log.Context, h vmextension.HandlerEnvironment, seqNum int) (
 		ctx = ctx.With("path", dataDir)
 		ctx.Log("event", "removing data dir", "path", dataDir)
 		if err := os.RemoveAll(dataDir); err != nil {
-			return "", errors.Wrap(err, "failed to delete data dir")
+			return "", errors.Wrap(err, "failed to delete data directory")
 		}
 		ctx.Log("event", "removed data dir")
 	}
@@ -128,9 +128,9 @@ func enablePre(ctx *log.Context, seqNum int) error {
 	// exit if this sequence number (a snapshot of the configuration) is already
 	// processed. if not, save this sequence number before proceeding.
 	if shouldExit, err := checkAndSaveSeqNum(ctx, seqNum, mostRecentSequence); err != nil {
-		return errors.Wrap(err, "failed to process seqnum")
+		return errors.Wrap(err, "failed to process sequence number")
 	} else if shouldExit {
-		ctx.Log("event", "exit", "message", "this script configuration is already processed, will not run again")
+		ctx.Log("event", "exit", "message", "the script configuration has already been processed, will not run again")
 		os.Exit(0)
 	}
 	return nil
@@ -197,7 +197,7 @@ func checkAndSaveSeqNum(ctx log.Logger, seq int, mrseqPath string) (shouldExit b
 		return true, nil
 	}
 	if err := seqnum.Set(mrseqPath, seq); err != nil {
-		return false, errors.Wrap(err, "failed to save the sequence number")
+		return false, errors.Wrap(err, "failed to save sequence number")
 	}
 	ctx.Log("event", "seqnum saved", "path", mrseqPath)
 	return false, nil
@@ -307,7 +307,7 @@ func writeTempScript(script, dir string, skipDosToUnix bool) (string, string, er
 	if skipDosToUnix == false {
 		err = postProcessFile(cmd)
 		if err != nil {
-			return "", "", errors.Wrap(err, "failed to post process file")
+			return "", "", errors.Wrap(err, "failed to post-process script.sh")
 		}
 		dos2unix = 0
 	}
@@ -319,7 +319,7 @@ func decodeScript(script string) (string, string, error) {
 	// scripts must be base64 encoded
 	s, err := base64.StdEncoding.DecodeString(script)
 	if err != nil {
-		return "", "", errors.Wrap(err, "failed to base64 decode script")
+		return "", "", errors.Wrap(err, "failed to decode script")
 	}
 
 	// scripts may be gzip'ed
diff --git a/main/files.go b/main/files.go
index 71dbb64..21cebe7 100644
--- a/main/files.go
+++ b/main/files.go
@@ -115,7 +115,7 @@ func urlToFileName(fileURL string) (string, error) {
 func postProcessFile(path string) error {
 	ok, err := preprocess.IsTextFile(path)
 	if err != nil {
-		return errors.Wrapf(err, "error determining if script file")
+		return errors.Wrapf(err, "error determining if script is a text file")
 	}
 	if !ok {
 		return nil
diff --git a/pkg/download/blobwithmsitoken.go b/pkg/download/blobwithmsitoken.go
index a5f59b5..6803e9e 100644
--- a/pkg/download/blobwithmsitoken.go
+++ b/pkg/download/blobwithmsitoken.go
@@ -36,7 +36,7 @@ func (self *blobWithMsiToken) GetRequest() (*http.Request, error) {
 		return nil, err
 	}
 	if msi.AccessToken == "" {
-		return nil, errors.New("MSI token was empty")
+		return nil, errors.New("MSI token is empty")
 	}
 
 	request, err := http.NewRequest(http.MethodGet, self.url, nil)
diff --git a/pkg/download/downloader.go b/pkg/download/downloader.go
index 45041c7..d5941bd 100644
--- a/pkg/download/downloader.go
+++ b/pkg/download/downloader.go
@@ -40,7 +40,7 @@ var (
 func Download(d Downloader) (int, io.ReadCloser, error) {
 	req, err := d.GetRequest()
 	if err != nil {
-		return -1, nil, errors.Wrapf(err, "failed to create the request")
+		return -1, nil, errors.Wrapf(err, "failed to create http request")
 	}
 
 	resp, err := httpClient.Do(req)