diff --git a/internal/provider/file/deploy.go b/internal/provider/file/deploy.go
index f46e28197..2807e7914 100644
--- a/internal/provider/file/deploy.go
+++ b/internal/provider/file/deploy.go
@@ -48,7 +48,7 @@ func (p *Service) Deploy(
 ) (*DeployResult, error) {
 	content, err := p.objStore.GetBytes(ctx, req.ObjectName)
 	if err != nil {
-		return nil, fmt.Errorf("failed to get object %q: %w", req.ObjectName, err)
+		return nil, fmt.Errorf("file deploy: get object %q: %w", req.ObjectName, err)
 	}
 
 	// When ContentType is not explicitly set, resolve it from the object's
@@ -69,7 +69,7 @@ func (p *Service) Deploy(
 	if contentType == "template" {
 		content, err = p.renderTemplate(content, req.Vars)
 		if err != nil {
-			return nil, fmt.Errorf("failed to render template: %w", err)
+			return nil, fmt.Errorf("file deploy: render template: %w", err)
 		}
 	}
 
@@ -117,11 +117,11 @@ func (p *Service) Deploy(
 
 	dir := p.fs.Dir(req.Path)
 	if err := p.fs.MkdirAll(dir, 0o755); err != nil {
-		return nil, fmt.Errorf("failed to create directory %q: %w", dir, err)
+		return nil, fmt.Errorf("file deploy: create directory %q: %w", dir, err)
 	}
 
 	if err := fsutil.WriteFileAtomic(p.fs, req.Path, content, mode); err != nil {
-		return nil, fmt.Errorf("failed to write file %q: %w", req.Path, err)
+		return nil, fmt.Errorf("file deploy: write file %q: %w", req.Path, err)
 	}
 
 	if _, err := p.enforceOwnership(ctx, req); err != nil {
@@ -170,12 +170,12 @@ func (p *Service) applyPermissions(
 
 		info, err := p.fs.Stat(req.Path)
 		if err != nil {
-			return false, fmt.Errorf("failed to stat file %q: %w", req.Path, err)
+			return false, fmt.Errorf("file deploy: stat file %q: %w", req.Path, err)
 		}
 
 		if info.Mode().Perm() != want.Perm() {
 			if err := p.fs.Chmod(req.Path, want); err != nil {
-				return false, fmt.Errorf("failed to set mode on %q: %w", req.Path, err)
+				return false, fmt.Errorf("file deploy: set mode on %q: %w", req.Path, err)
 			}
 
 			changed = true
@@ -202,17 +202,17 @@ func (p *Service) enforceOwnership(
 
 	wantUID, err := resolveID(req.Owner, lookupUID)
 	if err != nil {
-		return false, fmt.Errorf("failed to resolve owner for %q: %w", req.Path, err)
+		return false, fmt.Errorf("file deploy: resolve owner for %q: %w", req.Path, err)
 	}
 
 	wantGID, err := resolveID(req.Group, lookupGID)
 	if err != nil {
-		return false, fmt.Errorf("failed to resolve group for %q: %w", req.Path, err)
+		return false, fmt.Errorf("file deploy: resolve group for %q: %w", req.Path, err)
 	}
 
 	matches, err := ownershipMatches(req.Path, wantUID, wantGID)
 	if err != nil {
-		return false, fmt.Errorf("failed to read ownership of %q: %w", req.Path, err)
+		return false, fmt.Errorf("file deploy: read ownership of %q: %w", req.Path, err)
 	}
 
 	if matches {
@@ -232,7 +232,7 @@ func (p *Service) enforceOwnership(
 		[]string{spec, req.Path},
 	); err != nil {
 		return false, fmt.Errorf(
-			"failed to set ownership %q on %q: %w",
+			"file deploy: set ownership %q on %q: %w",
 			spec,
 			req.Path,
 			err,
@@ -264,11 +264,11 @@ func (p *Service) putState(
 
 	stateBytes, err := marshalJSON(state)
 	if err != nil {
-		return fmt.Errorf("failed to marshal file state: %w", err)
+		return fmt.Errorf("file deploy: marshal file state: %w", err)
 	}
 
 	if _, err := p.stateKV.Put(ctx, stateKey, stateBytes); err != nil {
-		return fmt.Errorf("failed to update file state: %w", err)
+		return fmt.Errorf("file deploy: update file state: %w", err)
 	}
 
 	return nil
diff --git a/internal/provider/file/deploy_public_test.go b/internal/provider/file/deploy_public_test.go
index bdbd8d517..0c5e88d1d 100644
--- a/internal/provider/file/deploy_public_test.go
+++ b/internal/provider/file/deploy_public_test.go
@@ -102,7 +102,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to marshal file state",
+			wantErrMsg: "file deploy: marshal file state",
 		},
 		{
 			name: "when deploy succeeds (new file)",
@@ -247,7 +247,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to get object",
+			wantErrMsg: "file deploy: get object",
 		},
 		{
 			name: "when content type is template",
@@ -391,7 +391,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to write file",
+			wantErrMsg: "file deploy: write file",
 		},
 		{
 			name: "when mkdir fails",
@@ -425,7 +425,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to create directory",
+			wantErrMsg: "file deploy: create directory",
 		},
 		{
 			name: "when state KV put fails",
@@ -449,7 +449,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to update file state",
+			wantErrMsg: "file deploy: update file state",
 		},
 		{
 			name: "when the mode cannot be parsed on a file already correct",
@@ -681,7 +681,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to resolve owner",
+			wantErrMsg: "file deploy: resolve owner",
 		},
 		{
 			name: "when the host does not know the requested group",
@@ -712,7 +712,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to resolve group",
+			wantErrMsg: "file deploy: resolve group",
 		},
 		{
 			name: "when the file ownership cannot be read at all",
@@ -743,7 +743,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to read ownership",
+			wantErrMsg: "file deploy: read ownership",
 		},
 		{
 			name: "when the platform cannot report ownership it is applied anyway",
@@ -888,7 +888,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to set ownership",
+			wantErrMsg: "file deploy: set ownership",
 		},
 		{
 			name: "when the file cannot be stat'd while enforcing the mode",
@@ -929,7 +929,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to stat file",
+			wantErrMsg: "file deploy: stat file",
 		},
 		{
 			name: "when the mode cannot be applied",
@@ -969,7 +969,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to set mode",
+			wantErrMsg: "file deploy: set mode",
 		},
 		{
 			name: "when chown fails on a file whose content is already correct",
@@ -1005,7 +1005,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to set ownership",
+			wantErrMsg: "file deploy: set ownership",
 		},
 		{
 			name: "when recording a permission change fails",
@@ -1033,7 +1033,7 @@ func (suite *DeployPublicTestSuite) TestDeploy() {
 				ContentType: "raw",
 			},
 			wantErr:    true,
-			wantErrMsg: "failed to update file state",
+			wantErrMsg: "file deploy: update file state",
 		},
 	}
 
diff --git a/internal/provider/file/status.go b/internal/provider/file/status.go
index 6959e2352..806e68210 100644
--- a/internal/provider/file/status.go
+++ b/internal/provider/file/status.go
@@ -47,7 +47,7 @@ func (p *Service) Status(
 
 	var state job.FileState
 	if err := json.Unmarshal(entry.Value(), &state); err != nil {
-		return nil, fmt.Errorf("failed to parse file state: %w", err)
+		return nil, fmt.Errorf("file status: parse file state: %w", err)
 	}
 
 	data, err := p.fs.ReadFile(req.Path)
diff --git a/internal/provider/file/status_public_test.go b/internal/provider/file/status_public_test.go
index 3a5b7a72f..6d362c7b0 100644
--- a/internal/provider/file/status_public_test.go
+++ b/internal/provider/file/status_public_test.go
@@ -183,7 +183,7 @@ func (suite *StatusPublicTestSuite) TestStatus() {
 			},
 			validateFunc: func(got *file.StatusResult, err error) {
 				suite.Error(err)
-				suite.ErrorContains(err, "failed to parse file state")
+				suite.ErrorContains(err, "file status: parse file state")
 				suite.Nil(got)
 			},
 		},
diff --git a/internal/provider/file/template.go b/internal/provider/file/template.go
index 5be71f266..e419a0338 100644
--- a/internal/provider/file/template.go
+++ b/internal/provider/file/template.go
@@ -44,7 +44,7 @@ func (p *Service) renderTemplate(
 ) ([]byte, error) {
 	tmpl, err := template.New("file").Option("missingkey=error").Parse(string(rawTemplate))
 	if err != nil {
-		return nil, fmt.Errorf("failed to parse template: %w", err)
+		return nil, fmt.Errorf("file template: parse template: %w", err)
 	}
 
 	ctx := TemplateContext{
@@ -55,7 +55,7 @@ func (p *Service) renderTemplate(
 
 	var buf bytes.Buffer
 	if err := tmpl.Execute(&buf, ctx); err != nil {
-		return nil, fmt.Errorf("failed to execute template: %w", err)
+		return nil, fmt.Errorf("file template: execute template: %w", err)
 	}
 
 	return buf.Bytes(), nil
diff --git a/internal/provider/file/template_public_test.go b/internal/provider/file/template_public_test.go
index d38d65254..a10269f74 100644
--- a/internal/provider/file/template_public_test.go
+++ b/internal/provider/file/template_public_test.go
@@ -166,7 +166,7 @@ func (suite *TemplatePublicTestSuite) TestDeployTemplate() {
 			wantErr:  true,
 			validateFunc: func(got *file.DeployResult, err error, _ avfs.VFS) {
 				suite.Error(err)
-				suite.ErrorContains(err, "failed to render template")
+				suite.ErrorContains(err, "file deploy: render template")
 				suite.Nil(got)
 			},
 		},
@@ -177,7 +177,7 @@ func (suite *TemplatePublicTestSuite) TestDeployTemplate() {
 			wantErr:  true,
 			validateFunc: func(got *file.DeployResult, err error, _ avfs.VFS) {
 				suite.Error(err)
-				suite.ErrorContains(err, "failed to render template")
+				suite.ErrorContains(err, "file deploy: render template")
 				suite.Nil(got)
 			},
 		},
@@ -189,7 +189,7 @@ func (suite *TemplatePublicTestSuite) TestDeployTemplate() {
 			wantErr:  true,
 			validateFunc: func(got *file.DeployResult, err error, _ avfs.VFS) {
 				suite.Error(err)
-				suite.ErrorContains(err, "failed to render template")
+				suite.ErrorContains(err, "file deploy: render template")
 				suite.Nil(got)
 			},
 		},
diff --git a/internal/provider/file/undeploy.go b/internal/provider/file/undeploy.go
index 6843fe2dd..c19c2f08e 100644
--- a/internal/provider/file/undeploy.go
+++ b/internal/provider/file/undeploy.go
@@ -51,7 +51,7 @@ func (p *Service) Undeploy(
 	}
 
 	if err := p.fs.Remove(req.Path); err != nil {
-		return nil, fmt.Errorf("failed to remove file %q: %w", req.Path, err)
+		return nil, fmt.Errorf("file undeploy: remove file %q: %w", req.Path, err)
 	}
 
 	stateKey := BuildStateKey(p.hostname, req.Path)
diff --git a/internal/provider/file/undeploy_public_test.go b/internal/provider/file/undeploy_public_test.go
index bac924f4b..3d8a9ecdb 100644
--- a/internal/provider/file/undeploy_public_test.go
+++ b/internal/provider/file/undeploy_public_test.go
@@ -195,7 +195,7 @@ func (suite *UndeployPublicTestSuite) TestUndeploy() {
 			},
 			req:        file.UndeployRequest{Path: "/etc/cron.d/locked"},
 			wantErr:    true,
-			wantErrMsg: "failed to remove file",
+			wantErrMsg: "file undeploy: remove file",
 			useFailFs:  true,
 		},
 		{