diff --git a/src/internal/converters/eml/eml.go b/src/internal/converters/eml/eml.go
index 41e737d2a..f8edeac4b 100644
--- a/src/internal/converters/eml/eml.go
+++ b/src/internal/converters/eml/eml.go
@@ -52,6 +52,8 @@ func formatAddress(entry models.EmailAddressable) string {
 
 // FromJSON converts a Messageable (as json) to .eml format
 func FromJSON(ctx context.Context, body []byte) (string, error) {
+	ctx = clues.Add(ctx, "body_len", len(body))
+
 	data, err := api.BytesToMessageable(body)
 	if err != nil {
 		return "", clues.WrapWC(ctx, err, "converting to messageble")
@@ -137,7 +139,8 @@ func FromJSON(ctx context.Context, body []byte) (string, error) {
 
 			bytes, err := attachment.GetBackingStore().Get("contentBytes")
 			if err != nil {
-				return "", clues.WrapWC(ctx, err, "failed to get attachment bytes")
+				return "", clues.WrapWC(ctx, err, "failed to get attachment bytes").
+					With("kind", kind)
 			}
 
 			if bytes == nil {
@@ -156,14 +159,17 @@ func FromJSON(ctx context.Context, body []byte) (string, error) {
 
 			bts, ok := bytes.([]byte)
 			if !ok {
-				return "", clues.WrapWC(ctx, err, "invalid content bytes")
+				return "", clues.WrapWC(ctx, err, "invalid content bytes").
+					With("kind", kind).
+					With("interface_type", fmt.Sprintf("%T", bytes))
 			}
 
 			name := ptr.Val(attachment.GetName())
 
 			contentID, err := attachment.GetBackingStore().Get("contentId")
 			if err != nil {
-				return "", clues.WrapWC(ctx, err, "getting content id for attachment")
+				return "", clues.WrapWC(ctx, err, "getting content id for attachment").
+					With("kind", kind)
 			}
 
 			if contentID != nil {
diff --git a/src/internal/converters/ics/ics.go b/src/internal/converters/ics/ics.go
index 7c1d1a760..a9d13d6bb 100644
--- a/src/internal/converters/ics/ics.go
+++ b/src/internal/converters/ics/ics.go
@@ -77,17 +77,18 @@ func getUTCTime(ts, tz string) (time.Time, error) {
 	// timezone everywhere according to the spec.
 	it, err := dttm.ParseTime(ts)
 	if err != nil {
-		return time.Now(), clues.Wrap(err, "parsing time")
+		return time.Time{}, clues.Wrap(err, "parsing time").With("given_time_string", ts)
 	}
 
 	timezone, ok := GraphTimeZoneToTZ[tz]
 	if !ok {
-		return it, clues.New("unknown timezone")
+		return it, clues.New("unknown timezone").With("timezone", tz)
 	}
 
 	loc, err := time.LoadLocation(timezone)
 	if err != nil {
-		return time.Now(), clues.Wrap(err, "loading timezone")
+		return time.Time{}, clues.Wrap(err, "loading timezone").
+			With("converted_timezone", timezone)
 	}
 
 	// embed timezone
@@ -170,7 +171,7 @@ func getRecurrencePattern(
 			if end != nil {
 				parsedTime, err := dttm.ParseTime(end.String())
 				if err != nil {
-					return "", clues.Wrap(err, "parsing recurrence end date")
+					return "", clues.Wrap(err, "parsing recurrence end date").With("recur_end_date", end.String())
 				}
 
 				// end date is always computed as end of the day and
@@ -203,7 +204,8 @@ func getRecurrencePattern(
 func FromJSON(ctx context.Context, body []byte) (string, error) {
 	event, err := api.BytesToEventable(body)
 	if err != nil {
-		return "", clues.WrapWC(ctx, err, "converting to eventable")
+		return "", clues.WrapWC(ctx, err, "converting to eventable").
+			With("body_len", len(body))
 	}
 
 	cal := ics.NewCalendar()
@@ -231,7 +233,8 @@ func FromJSON(ctx context.Context, body []byte) (string, error) {
 
 		exBody, err := json.Marshal(instance)
 		if err != nil {
-			return "", clues.WrapWC(ctx, err, "marshalling exception instance")
+			return "", clues.WrapWC(ctx, err, "marshalling exception instance").
+				With("instance_id", instance["id"])
 		}
 
 		exception, err := api.BytesToEventable(exBody)
@@ -363,7 +366,8 @@ func updateEventProperties(ctx context.Context, event models.Eventable, iCalEven
 				} else {
 					stripped, err := html2text.FromString(description, html2text.Options{PrettyTables: true})
 					if err != nil {
-						return clues.Wrap(err, "converting html to text")
+						return clues.Wrap(err, "converting html to text").
+							With("description_length", len(description))
 					}
 
 					iCalEvent.SetDescription(stripped)
@@ -534,7 +538,8 @@ func updateEventProperties(ctx context.Context, event models.Eventable, iCalEven
 
 		content, ok := cb.([]uint8)
 		if !ok {
-			return clues.NewWC(ctx, "getting attachment content string")
+			return clues.NewWC(ctx, "getting attachment content string").
+				With("interface_type", fmt.Sprintf("%T", cb))
 		}
 
 		props = append(props, ics.WithEncoding("base64"), ics.WithValue("BINARY"))
@@ -553,7 +558,8 @@ func updateEventProperties(ctx context.Context, event models.Eventable, iCalEven
 
 			cid, err := str.AnyToString(cidv)
 			if err != nil {
-				return clues.WrapWC(ctx, err, "getting attachment content id string")
+				return clues.WrapWC(ctx, err, "getting attachment content id string").
+					With("interface_type", fmt.Sprintf("%T", cidv))
 			}
 
 			props = append(props, keyValues("CID", cid))
@@ -565,7 +571,8 @@ func updateEventProperties(ctx context.Context, event models.Eventable, iCalEven
 	// EXDATE - https://www.rfc-editor.org/rfc/rfc5545#section-3.8.5.1
 	cancelledDates, err := getCancelledDates(ctx, event)
 	if err != nil {
-		return clues.Wrap(err, "getting cancelled dates")
+		return clues.Wrap(err, "getting cancelled dates").
+			With("event_id", event.GetId())
 	}
 
 	dateStrings := []string{}
diff --git a/src/internal/converters/vcf/vcf.go b/src/internal/converters/vcf/vcf.go
index aa0785cf9..0a6a44b2a 100644
--- a/src/internal/converters/vcf/vcf.go
+++ b/src/internal/converters/vcf/vcf.go
@@ -86,7 +86,8 @@ func FromJSON(ctx context.Context, body []byte) (string, error) {
 
 	data, err := api.BytesToContactable(body)
 	if err != nil {
-		return "", clues.Wrap(err, "converting to contactable")
+		return "", clues.Wrap(err, "converting to contactable").
+			With("body_length", len(body))
 	}
 
 	name := vcard.Name{
diff --git a/src/pkg/services/m365/api/events.go b/src/pkg/services/m365/api/events.go
index 8f36051f5..6f197e93c 100644
--- a/src/pkg/services/m365/api/events.go
+++ b/src/pkg/services/m365/api/events.go
@@ -338,7 +338,9 @@ func GetCancelledEventDateStrings(event models.Eventable) ([]string, error) {
 
 		_, err = dttm.ParseTime(startStr)
 		if err != nil {
-			return nil, clues.Wrap(err, "parsing cancelled event date")
+			return nil, clues.Wrap(err, "parsing cancelled event date").
+				With("instance", instance).
+				With("start_string", startStr)
 		}
 
 		dates = append(dates, startStr)