diff --git a/server/prompt_test.go b/server/prompt_test.go
index d4cee98c..1435b143 100644
--- a/server/prompt_test.go
+++ b/server/prompt_test.go
@@ -161,7 +161,7 @@ func TestChatPrompt(t *testing.T) {
 				{Role: "user", Content: "A test. And a thumping good one at that, I'd wager."},
 			},
 			expect: expect{
-				prompt: "You're a test, Harry! I-I'm a what? You are the Test Who Lived. A test. And a thumping good one at that, I'd wager. ",
+				prompt: "You are the Test Who Lived. You're a test, Harry! I-I'm a what? A test. And a thumping good one at that, I'd wager. ",
 			},
 		},
 	}
diff --git a/server/routes_create_test.go b/server/routes_create_test.go
index 269a0ba1..40477937 100644
--- a/server/routes_create_test.go
+++ b/server/routes_create_test.go
@@ -546,8 +546,8 @@ func TestCreateDetectTemplate(t *testing.T) {
 
 		checkFileExists(t, filepath.Join(p, "blobs", "*"), []string{
 			filepath.Join(p, "blobs", "sha256-553c4a3f747b3d22a4946875f1cc8ed011c2930d83f864a0c7265f9ec0a20413"),
-			filepath.Join(p, "blobs", "sha256-9512c372dfc7d84d6065b8dd2b601aeed8cc1a78e7a7aa784a42fff37f5524b7"),
-			filepath.Join(p, "blobs", "sha256-b8b78cb8c6eefd14c06f1af042e6161255bf87bbf2dd14fce57cdac893db8139"),
+			filepath.Join(p, "blobs", "sha256-68b0323b2f21572bc09ba07554b16b379a5713ee48ef8c25a7661a1f71cfce77"),
+			filepath.Join(p, "blobs", "sha256-eb72fb7c550ee1f1dec4039bd65382acecf5f7536a30fb7ccace39a8d0cb590b"),
 		})
 	})
 
diff --git a/template/template.go b/template/template.go
index b133b97e..0b8f2434 100644
--- a/template/template.go
+++ b/template/template.go
@@ -143,11 +143,14 @@ func (t *Template) Vars() []string {
 
 type Values struct {
 	Messages []api.Message
+
+	// forceLegacy is a flag used to test compatibility with legacy templates
+	forceLegacy bool
 }
 
 func (t *Template) Execute(w io.Writer, v Values) error {
 	system, collated := collate(v.Messages)
-	if slices.Contains(t.Vars(), "messages") {
+	if !v.forceLegacy && slices.Contains(t.Vars(), "messages") {
 		return t.Template.Execute(w, map[string]any{
 			"System":   system,
 			"Messages": collated,
@@ -157,15 +160,19 @@ func (t *Template) Execute(w io.Writer, v Values) error {
 	var b bytes.Buffer
 	var prompt, response string
 	for i, m := range collated {
-		if m.Role == "user" {
+		switch m.Role {
+		case "user":
 			prompt = m.Content
-		} else {
+			if i != 0 {
+				system = ""
+			}
+		case "assistant":
 			response = m.Content
 		}
 
 		if i != len(collated)-1 && prompt != "" && response != "" {
 			if err := t.Template.Execute(&b, map[string]any{
-				"System":   "",
+				"System":   system,
 				"Prompt":   prompt,
 				"Response": response,
 			}); err != nil {
@@ -178,18 +185,21 @@ func (t *Template) Execute(w io.Writer, v Values) error {
 	}
 
 	var cut bool
-	tree := t.Template.Copy()
-	// for the last message, cut everything after "{{ .Response }}"
-	tree.Root.Nodes = slices.DeleteFunc(tree.Root.Nodes, func(n parse.Node) bool {
-		if slices.Contains(parseNode(n), "Response") {
-			cut = true
+	nodes := deleteNode(t.Template.Root.Copy(), func(n parse.Node) bool {
+		switch t := n.(type) {
+		case *parse.ActionNode:
+		case *parse.FieldNode:
+			if slices.Contains(t.Ident, "Response") {
+				cut = true
+			}
 		}
 
 		return cut
 	})
 
-	if err := template.Must(template.New("").AddParseTree("", tree)).Execute(&b, map[string]any{
-		"System": system,
+	tree := parse.Tree{Root: nodes.(*parse.ListNode)}
+	if err := template.Must(template.New("").AddParseTree("", &tree)).Execute(&b, map[string]any{
+		"System": "",
 		"Prompt": prompt,
 	}); err != nil {
 		return err
@@ -286,3 +296,72 @@ func parseNode(n parse.Node) []string {
 
 	return nil
 }
+
+// deleteNode walks the node list and deletes nodes that match the predicate
+// this is currently to remove the {{ .Response }} node from templates
+func deleteNode(n parse.Node, fn func(parse.Node) bool) parse.Node {
+	var walk func(n parse.Node) parse.Node
+	walk = func(n parse.Node) parse.Node {
+		if fn(n) {
+			return nil
+		}
+
+		switch t := n.(type) {
+		case *parse.ListNode:
+			var nodes []parse.Node
+			for _, c := range t.Nodes {
+				if n := walk(c); n != nil {
+					nodes = append(nodes, n)
+				}
+			}
+
+			t.Nodes = nodes
+			return t
+		case *parse.IfNode:
+			t.BranchNode = *(walk(&t.BranchNode).(*parse.BranchNode))
+		case *parse.WithNode:
+			t.BranchNode = *(walk(&t.BranchNode).(*parse.BranchNode))
+		case *parse.RangeNode:
+			t.BranchNode = *(walk(&t.BranchNode).(*parse.BranchNode))
+		case *parse.BranchNode:
+			t.List = walk(t.List).(*parse.ListNode)
+			if t.ElseList != nil {
+				t.ElseList = walk(t.ElseList).(*parse.ListNode)
+			}
+		case *parse.ActionNode:
+			n := walk(t.Pipe)
+			if n == nil {
+				return nil
+			}
+
+			t.Pipe = n.(*parse.PipeNode)
+		case *parse.PipeNode:
+			var commands []*parse.CommandNode
+			for _, c := range t.Cmds {
+				var args []parse.Node
+				for _, a := range c.Args {
+					if n := walk(a); n != nil {
+						args = append(args, n)
+					}
+				}
+
+				if len(args) == 0 {
+					return nil
+				}
+
+				c.Args = args
+				commands = append(commands, c)
+			}
+
+			if len(commands) == 0 {
+				return nil
+			}
+
+			t.Cmds = commands
+		}
+
+		return n
+	}
+
+	return walk(n)
+}
diff --git a/template/template_test.go b/template/template_test.go
index 428cdc77..e702a186 100644
--- a/template/template_test.go
+++ b/template/template_test.go
@@ -105,8 +105,8 @@ func TestTemplate(t *testing.T) {
 			}
 
 			for n, tt := range cases {
+				var actual bytes.Buffer
 				t.Run(n, func(t *testing.T) {
-					var actual bytes.Buffer
 					if err := tmpl.Execute(&actual, Values{Messages: tt}); err != nil {
 						t.Fatal(err)
 					}
@@ -120,6 +120,25 @@ func TestTemplate(t *testing.T) {
 						t.Errorf("mismatch (-got +want):\n%s", diff)
 					}
 				})
+
+				t.Run("legacy", func(t *testing.T) {
+					var legacy bytes.Buffer
+					if err := tmpl.Execute(&legacy, Values{Messages: tt, forceLegacy: true}); err != nil {
+						t.Fatal(err)
+					}
+
+					legacyBytes := legacy.Bytes()
+					if slices.Contains([]string{"chatqa.gotmpl", "openchat.gotmpl", "vicuna.gotmpl"}, match) && legacyBytes[len(legacyBytes)-1] == ' ' {
+						t.Log("removing trailing space from legacy output")
+						legacyBytes = legacyBytes[:len(legacyBytes)-1]
+					} else if slices.Contains([]string{"codellama-70b-instruct.gotmpl", "llama2-chat.gotmpl", "mistral-instruct.gotmpl"}, match) {
+						t.Skip("legacy outputs cannot be compared to messages outputs")
+					}
+
+					if diff := cmp.Diff(legacyBytes, actual.Bytes()); diff != "" {
+						t.Errorf("mismatch (-got +want):\n%s", diff)
+					}
+				})
 			}
 		})
 	}
@@ -136,6 +155,21 @@ func TestParse(t *testing.T) {
 		{"{{ with .Tools }}{{ . }}{{ end }} {{ .System }} {{ .Prompt }}", []string{"prompt", "response", "system", "tools"}},
 		{"{{ range .Messages }}{{ .Role }} {{ .Content }}{{ end }}", []string{"content", "messages", "role"}},
 		{"{{ range .Messages }}{{ if eq .Role \"system\" }}SYSTEM: {{ .Content }}{{ else if eq .Role \"user\" }}USER: {{ .Content }}{{ else if eq .Role \"assistant\" }}ASSISTANT: {{ .Content }}{{ end }}{{ end }}", []string{"content", "messages", "role"}},
+		{`{{- if .Messages }}
+{{- if .System }}<|im_start|>system
+{{ .System }}<|im_end|>
+{{ end }}
+{{- range .Messages }}<|im_start|>{{ .Role }}
+{{ .Content }}<|im_end|>
+{{ end }}<|im_start|>assistant
+{{ else -}}
+{{ if .System }}<|im_start|>system
+{{ .System }}<|im_end|>
+{{ end }}{{ if .Prompt }}<|im_start|>user
+{{ .Prompt }}<|im_end|>
+{{ end }}<|im_start|>assistant
+{{ .Response }}<|im_end|>
+{{- end -}}`, []string{"content", "messages", "prompt", "response", "role", "system"}},
 	}
 
 	for _, tt := range cases {
@@ -145,9 +179,8 @@ func TestParse(t *testing.T) {
 				t.Fatal(err)
 			}
 
-			vars := tmpl.Vars()
-			if !slices.Equal(tt.vars, vars) {
-				t.Errorf("expected %v, got %v", tt.vars, vars)
+			if diff := cmp.Diff(tmpl.Vars(), tt.vars); diff != "" {
+				t.Errorf("mismatch (-got +want):\n%s", diff)
 			}
 		})
 	}
@@ -170,7 +203,7 @@ func TestExecuteWithMessages(t *testing.T) {
 				{"no response", `[INST] {{ if .System }}{{ .System }}{{ "\n\n" }}{{ end }}{{ .Prompt }}[/INST] `},
 				{"response", `[INST] {{ if .System }}{{ .System }}{{ "\n\n" }}{{ end }}{{ .Prompt }}[/INST] {{ .Response }}`},
 				{"messages", `{{- range $index, $_ := .Messages }}
-{{- if eq .Role "user" }}[INST] {{ if and (eq (len (slice $.Messages $index)) 1) $.System }}{{ $.System }}{{ "\n\n" }}
+{{- if eq .Role "user" }}[INST] {{ if and (eq $index 0) $.System }}{{ $.System }}{{ "\n\n" }}
 {{- end }}{{ .Content }}[/INST] {{ else if eq .Role "assistant" }}{{ .Content }}
 {{- end }}
 {{- end }}`},
@@ -191,7 +224,7 @@ func TestExecuteWithMessages(t *testing.T) {
 				{"response", `[INST] {{ if .System }}{{ .System }}{{ "\n\n" }}{{ end }}{{ .Prompt }}[/INST] {{ .Response }}`},
 				{"messages", `
 {{- range $index, $_ := .Messages }}
-{{- if eq .Role "user" }}[INST] {{ if and (eq (len (slice $.Messages $index)) 1) $.System }}{{ $.System }}{{ "\n\n" }}
+{{- if eq .Role "user" }}[INST] {{ if and (eq $index 0) $.System }}{{ $.System }}{{ "\n\n" }}
 {{- end }}{{ .Content }}[/INST] {{ else if eq .Role "assistant" }}{{ .Content }}
 {{- end }}
 {{- end }}`},
@@ -204,9 +237,9 @@ func TestExecuteWithMessages(t *testing.T) {
 					{Role: "user", Content: "What is your name?"},
 				},
 			},
-			`[INST] Hello friend![/INST] Hello human![INST] You are a helpful assistant!
+			`[INST] You are a helpful assistant!
 
-What is your name?[/INST] `,
+Hello friend![/INST] Hello human![INST] What is your name?[/INST] `,
 		},
 		{
 			"chatml",
@@ -221,7 +254,7 @@ What is your name?[/INST] `,
 `},
 				{"messages", `
 {{- range $index, $_ := .Messages }}
-{{- if and (eq .Role "user") (eq (len (slice $.Messages $index)) 1) $.System }}<|im_start|>system
+{{- if and (eq .Role "user") (eq $index 0) $.System }}<|im_start|>system
 {{ $.System }}<|im_end|>{{ "\n" }}
 {{- end }}<|im_start|>{{ .Role }}
 {{ .Content }}<|im_end|>{{ "\n" }}
@@ -236,12 +269,12 @@ What is your name?[/INST] `,
 					{Role: "user", Content: "What is your name?"},
 				},
 			},
-			`<|im_start|>user
+			`<|im_start|>system
+You are a helpful assistant!<|im_end|>
+<|im_start|>user
 Hello friend!<|im_end|>
 <|im_start|>assistant
 Hello human!<|im_end|>
-<|im_start|>system
-You are a helpful assistant!<|im_end|>
 <|im_start|>user
 What is your name?<|im_end|>
 <|im_start|>assistant
@@ -300,8 +333,8 @@ Answer: `,
 						t.Fatal(err)
 					}
 
-					if b.String() != tt.expected {
-						t.Errorf("expected\n%s,\ngot\n%s", tt.expected, b.String())
+					if diff := cmp.Diff(b.String(), tt.expected); diff != "" {
+						t.Errorf("mismatch (-got +want):\n%s", diff)
 					}
 				})
 			}