diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index c83252be2..ccd6a2fdb 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -511,6 +511,13 @@ jobs:
             echo "Use len check instead of empty string comparison"
             exit 1
           fi
+      - name: Check for cases where errors are not propagated
+        run: |
+          # Using `grep .` as the exit codes are always true for correct grammar
+          if tree-grepper -q go '((if_statement (binary_expression) @_if (block (return_statement (expression_list (call_expression (selector_expression) @_fun ) @ret .)))) (#match? @_if "err != nil") (#match? @_fun "clues.NewWC"))' | grep .; then
+            echo "Make sure to propagate errors with clues"
+            exit 1
+          fi
 
   # ----------------------------------------------------------------------------------------------------
   # --- GitHub Actions Linting -------------------------------------------------------------------------
diff --git a/src/internal/kopia/upload.go b/src/internal/kopia/upload.go
index d70fb0152..171b0cae6 100644
--- a/src/internal/kopia/upload.go
+++ b/src/internal/kopia/upload.go
@@ -1204,12 +1204,12 @@ func traverseBaseDir(
 
 		curP, err := path.PrefixOrPathFromDataLayerPath(currentPath.String(), false)
 		if err != nil {
-			return clues.NewWC(ctx, "converting current path to path.Path")
+			return clues.WrapWC(ctx, err, "converting current path to path.Path")
 		}
 
 		oldP, err := path.PrefixOrPathFromDataLayerPath(oldDirPath.String(), false)
 		if err != nil {
-			return clues.NewWC(ctx, "converting old path to path.Path")
+			return clues.WrapWC(ctx, err, "converting old path to path.Path")
 		}
 
 		node.baseDir = dir
diff --git a/src/internal/m365/collection/drive/permission.go b/src/internal/m365/collection/drive/permission.go
index 8718b63bf..2eb19c054 100644
--- a/src/internal/m365/collection/drive/permission.go
+++ b/src/internal/m365/collection/drive/permission.go
@@ -98,7 +98,7 @@ func computePreviousLinkShares(
 
 	parent, err := originDir.Dir()
 	if err != nil {
-		return nil, clues.NewWC(ctx, "getting parent")
+		return nil, clues.WrapWC(ctx, err, "getting parent")
 	}
 
 	for len(parent.Elements()) > 0 {
@@ -106,7 +106,7 @@ func computePreviousLinkShares(
 
 		drivePath, err := path.ToDrivePath(parent)
 		if err != nil {
-			return nil, clues.NewWC(ictx, "transforming dir to drivePath")
+			return nil, clues.WrapWC(ictx, err, "transforming dir to drivePath")
 		}
 
 		if len(drivePath.Folders) == 0 {
@@ -126,7 +126,7 @@ func computePreviousLinkShares(
 
 		parent, err = parent.Dir()
 		if err != nil {
-			return nil, clues.NewWC(ictx, "getting parent")
+			return nil, clues.WrapWC(ictx, err, "getting parent")
 		}
 	}
 
@@ -156,14 +156,14 @@ func computePreviousMetadata(
 	for {
 		parent, err = parent.Dir()
 		if err != nil {
-			return metadata.Metadata{}, clues.NewWC(ctx, "getting parent")
+			return metadata.Metadata{}, clues.WrapWC(ctx, err, "getting parent")
 		}
 
 		ictx := clues.Add(ctx, "parent_dir", parent)
 
 		drivePath, err := path.ToDrivePath(parent)
 		if err != nil {
-			return metadata.Metadata{}, clues.NewWC(ictx, "transforming dir to drivePath")
+			return metadata.Metadata{}, clues.WrapWC(ictx, err, "transforming dir to drivePath")
 		}
 
 		if len(drivePath.Folders) == 0 {
diff --git a/src/internal/m365/collection/exchange/metadata.go b/src/internal/m365/collection/exchange/metadata.go
index dbd20e146..2ca9eced4 100644
--- a/src/internal/m365/collection/exchange/metadata.go
+++ b/src/internal/m365/collection/exchange/metadata.go
@@ -63,7 +63,7 @@ func ParseMetadataCollections(
 
 				err := json.NewDecoder(item.ToReader()).Decode(&m)
 				if err != nil {
-					return nil, false, clues.NewWC(ctx, "decoding metadata json")
+					return nil, false, clues.WrapWC(ctx, err, "decoding metadata json")
 				}
 
 				switch item.ID() {
diff --git a/src/internal/m365/collection/groups/metadata.go b/src/internal/m365/collection/groups/metadata.go
index 9c196c348..4f123945f 100644
--- a/src/internal/m365/collection/groups/metadata.go
+++ b/src/internal/m365/collection/groups/metadata.go
@@ -64,7 +64,7 @@ func parseMetadataCollections(
 
 				err := json.NewDecoder(item.ToReader()).Decode(&m)
 				if err != nil {
-					return nil, false, clues.NewWC(ctx, "decoding metadata json")
+					return nil, false, clues.WrapWC(ctx, err, "decoding metadata json")
 				}
 
 				switch item.ID() {
diff --git a/src/internal/operations/backup.go b/src/internal/operations/backup.go
index 1a544caa5..95fd95c26 100644
--- a/src/internal/operations/backup.go
+++ b/src/internal/operations/backup.go
@@ -673,7 +673,7 @@ func mergeItemsFromBase(
 		errs)
 	if err != nil {
 		return manifestAddedEntries,
-			clues.NewWC(ctx, "fetching base details for backup")
+			clues.WrapWC(ctx, err, "fetching base details for backup")
 	}
 
 	for _, entry := range baseDeets.Items() {
@@ -683,7 +683,7 @@ func mergeItemsFromBase(
 
 		rr, err := path.FromDataLayerPath(entry.RepoRef, true)
 		if err != nil {
-			return manifestAddedEntries, clues.NewWC(ctx, "parsing base item info path").
+			return manifestAddedEntries, clues.WrapWC(ctx, err, "parsing base item info path").
 				With("repo_ref", path.LoggableDir(entry.RepoRef))
 		}