diff --git a/hack/gen-catalog/main.go b/hack/gen-catalog/main.go
index ff3da21d6791d..c7963dbf83ab4 100644
--- a/hack/gen-catalog/main.go
+++ b/hack/gen-catalog/main.go
@@ -168,7 +168,7 @@ func generateCommandsDocs(out io.Writer) error {
 				for _, c := range toolSubCommand.Commands() {
 					var cmdDesc bytes.Buffer
 					if err := doc.GenMarkdown(c, &cmdDesc); err != nil {
-						return err
+						return fmt.Errorf("error generating Markdown for command: %v : %w", c, err)
 					}
 					for _, line := range strings.Split(cmdDesc.String(), "\n") {
 						if strings.HasPrefix(line, "### SEE ALSO") {
@@ -194,19 +194,19 @@ func buildConfigFromFS(templatesDir string, triggersDir string) (map[string]serv
 	templatesCfg := map[string]services.Notification{}
 	err := filepath.Walk(templatesDir, func(p string, info os.FileInfo, e error) error {
 		if e != nil {
-			return e
+			return fmt.Errorf("error navigating the templates dirctory: %s : %w", templatesDir, e)
 		}
 		if info.IsDir() {
 			return nil
 		}
 		data, err := os.ReadFile(p)
 		if err != nil {
-			return err
+			return fmt.Errorf("error reading the template file: %s : %w", p, err)
 		}
 		name := strings.Split(path.Base(p), ".")[0]
 		var template services.Notification
 		if err := yaml.Unmarshal(data, &template); err != nil {
-			return err
+			return fmt.Errorf("error unmarshaling the data from file: %s : %w", p, err)
 		}
 		templatesCfg[name] = template
 		return nil
@@ -218,19 +218,19 @@ func buildConfigFromFS(templatesDir string, triggersDir string) (map[string]serv
 	triggersCfg := map[string][]triggers.Condition{}
 	err = filepath.Walk(triggersDir, func(p string, info os.FileInfo, e error) error {
 		if e != nil {
-			return e
+			return fmt.Errorf("error navigating the triggers dirctory: %s : %w", triggersDir, e)
 		}
 		if info.IsDir() {
 			return nil
 		}
 		data, err := os.ReadFile(p)
 		if err != nil {
-			return err
+			return fmt.Errorf("error reading the trigger file: %s : %w", p, err)
 		}
 		name := strings.Split(path.Base(p), ".")[0]
 		var trigger []triggers.Condition
 		if err := yaml.Unmarshal(data, &trigger); err != nil {
-			return err
+			return fmt.Errorf("error unmarshaling the data from file: %s : %w", p, err)
 		}
 		triggersCfg[name] = trigger
 		return nil
diff --git a/hack/gen-docs/main.go b/hack/gen-docs/main.go
index c641e833417d3..c39f4628a432c 100644
--- a/hack/gen-docs/main.go
+++ b/hack/gen-docs/main.go
@@ -37,7 +37,7 @@ func updateMkDocsNav(parent string, child string, subchild string, files []strin
 	sort.Strings(files)
 	data, err := os.ReadFile("mkdocs.yml")
 	if err != nil {
-		return err
+		return fmt.Errorf("error reading mkdocs.yml: %w", err)
 	}
 	var un unstructured.Unstructured
 	if e := yaml.Unmarshal(data, &un.Object); e != nil {
@@ -46,12 +46,12 @@ func updateMkDocsNav(parent string, child string, subchild string, files []strin
 	nav := un.Object["nav"].([]interface{})
 	rootitem, _ := findNavItem(nav, parent)
 	if rootitem == nil {
-		return fmt.Errorf("Can't find '%s' root item in mkdoc.yml", parent)
+		return fmt.Errorf("can't find '%s' root item in mkdoc.yml", parent)
 	}
 	rootnavitemmap := rootitem.(map[interface{}]interface{})
 	childnav, _ := findNavItem(rootnavitemmap[parent].([]interface{}), child)
 	if childnav == nil {
-		return fmt.Errorf("Can't find '%s' chile item under '%s' parent item in mkdoc.yml", child, parent)
+		return fmt.Errorf("can't find '%s' chile item under '%s' parent item in mkdoc.yml", child, parent)
 	}
 
 	childnavmap := childnav.(map[interface{}]interface{})
@@ -63,7 +63,7 @@ func updateMkDocsNav(parent string, child string, subchild string, files []strin
 	childnavmap[child] = append(childnavitems, commands)
 	newmkdocs, err := yaml.Marshal(un.Object)
 	if err != nil {
-		return err
+		return fmt.Errorf("error in marshaling final configmap: %w", err)
 	}
 
 	// The marshaller drops custom tags, so re-add this one. Turns out this is much less invasive than trying to handle
diff --git a/hack/gen-resources/util/gen_options_parser.go b/hack/gen-resources/util/gen_options_parser.go
index 8446dd5c07754..22c36ab661a58 100644
--- a/hack/gen-resources/util/gen_options_parser.go
+++ b/hack/gen-resources/util/gen_options_parser.go
@@ -1,6 +1,7 @@
 package util
 
 import (
+	"fmt"
 	"os"
 
 	"gopkg.in/yaml.v2"
@@ -55,7 +56,7 @@ func setDefaults(opts *GenerateOpts) {
 func Parse(opts *GenerateOpts, file string) error {
 	fp, err := os.ReadFile(file)
 	if err != nil {
-		return err
+		return fmt.Errorf("error reading the template file: %s : %w", file, err)
 	}
 
 	if e := yaml.Unmarshal(fp, &opts); e != nil {
diff --git a/hack/known_types/main.go b/hack/known_types/main.go
index e6647396c3c39..247fadffd908c 100644
--- a/hack/known_types/main.go
+++ b/hack/known_types/main.go
@@ -42,7 +42,7 @@ func newCommand() *cobra.Command {
 			imprt := importer.ForCompiler(token.NewFileSet(), "source", nil)
 			pkg, err := imprt.Import(packagePath)
 			if err != nil {
-				return err
+				return fmt.Errorf("error while importing the package at: %s : %w", packagePath, err)
 			}
 
 			shortPackagePath := strings.TrimPrefix(packagePath, packagePrefix)
@@ -78,7 +78,7 @@ func init() {%s
 }`, strings.Join(mapItems, ""))
 			if docsOutputPath != "" {
 				if err = os.WriteFile(docsOutputPath, []byte(strings.Join(docs, "\n")), 0o644); err != nil {
-					return err
+					return fmt.Errorf("error while writing to the %s: %w", docsOutputPath, err)
 				}
 			}