diff --git a/backend/pkg/providers/helpers.go b/backend/pkg/providers/helpers.go
index e040b953..1445e575 100644
--- a/backend/pkg/providers/helpers.go
+++ b/backend/pkg/providers/helpers.go
@@ -44,6 +44,33 @@ type dummyMessage struct {
 	Message string `json:"message"`
 }
 
+// wrapToolCallIDTemplateError annotates an error returned by
+// Provider.GetToolCallIDTemplate so the user sees an actionable hint when a
+// known upstream limitation blocks provider initialization. Currently it
+// covers the Ollama "model does not support tools" case (issue #280): the
+// underlying error is returned by the Ollama API itself and surfaces five
+// wraps deep, which previously left the user with a cryptic "failed to
+// determine tool call ID template" message. This helper is shared by the
+// flow and assistant provider paths, so the wording stays context-neutral.
+//
+// The function preserves the original error chain via %w so downstream code
+// (logs, langfuse spans, errors.Is/As) keeps working.
+func wrapToolCallIDTemplateError(err error) error {
+	if err == nil {
+		return nil
+	}
+	if strings.Contains(err.Error(), "does not support tools") {
+		return fmt.Errorf(
+			"failed to determine tool call ID template: the selected model "+
+				"does not support tool/function calling, which PentAGI requires "+
+				"for tool execution in flows and assistant sessions; select an "+
+				"Ollama model whose metadata advertises tool/function calling "+
+				"support and update the provider configuration: %w",
+			err)
+	}
+	return fmt.Errorf("failed to determine tool call ID template: %w", err)
+}
+
 type reflectorRetryContextKey struct{}
 
 // isReflectorRetry checks if we are already in a reflector retry cycle
diff --git a/backend/pkg/providers/helpers_test.go b/backend/pkg/providers/helpers_test.go
index 1b5e201a..1b4099b8 100644
--- a/backend/pkg/providers/helpers_test.go
+++ b/backend/pkg/providers/helpers_test.go
@@ -2,7 +2,10 @@ package providers
 
 import (
 	"encoding/json"
+	"errors"
+	"fmt"
 	"slices"
+	"strings"
 	"sync"
 	"sync/atomic"
 	"testing"
@@ -1174,3 +1177,99 @@ func TestExecutionMonitorDetector_TotalCallsSequence(t *testing.T) {
 func mockToolCall(name string) llms.ToolCall {
 	return llms.ToolCall{FunctionCall: &llms.FunctionCall{Name: name}}
 }
+
+func TestWrapToolCallIDTemplateError(t *testing.T) {
+	t.Parallel()
+
+	// Mirror the real upstream wrap chain so the test traps regressions in
+	// substring detection if the inner wraps ever change.
+	ollamaErr := fmt.Errorf(
+		"all sample collection attempts failed: %w",
+		fmt.Errorf("failed to call LLM: %w",
+			errors.New("400 Bad Request: registry.ollama.ai/library/gemma3:27b-it-q4_K_M does not support tools")),
+	)
+	genericErr := errors.New("connection refused")
+
+	cases := []struct {
+		name           string
+		input          error
+		wantNil        bool
+		wantContains   []string
+		wantUnwrapsTo  error
+		wantNotContain []string
+	}{
+		{
+			name:    "nil error passes through",
+			input:   nil,
+			wantNil: true,
+		},
+		{
+			name:  "ollama tools error gets actionable hint",
+			input: ollamaErr,
+			wantContains: []string{
+				"failed to determine tool call ID template",
+				"does not support tool/function calling",
+				"PentAGI requires",
+				"flows and assistant sessions",
+				"metadata advertises tool/function calling",
+				"does not support tools",
+			},
+			wantNotContain: []string{
+				// The hint must not name specific model tags as
+				// tool-capable, because Ollama model capabilities are
+				// not verified by PentAGI and any concrete list ages
+				// poorly.
+				"llama3.1",
+				"qwen2.5",
+				"mistral-nemo",
+				// The helper is shared by both the flow and assistant
+				// provider paths, so the message must not imply this
+				// is a flow-only failure mode.
+				"flow execution",
+				"flow creation",
+			},
+			wantUnwrapsTo: ollamaErr,
+		},
+		{
+			name:  "non-tools error keeps existing wrap",
+			input: genericErr,
+			wantContains: []string{
+				"failed to determine tool call ID template",
+				"connection refused",
+			},
+			wantNotContain: []string{
+				"does not support tool/function calling",
+				"metadata advertises tool/function calling",
+			},
+			wantUnwrapsTo: genericErr,
+		},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			got := wrapToolCallIDTemplateError(tc.input)
+			if tc.wantNil {
+				assert.Nil(t, got)
+				return
+			}
+			if !assert.NotNil(t, got) {
+				return
+			}
+			msg := got.Error()
+			for _, want := range tc.wantContains {
+				assert.Truef(t, strings.Contains(msg, want),
+					"expected error message to contain %q; got %q", want, msg)
+			}
+			for _, banned := range tc.wantNotContain {
+				assert.Falsef(t, strings.Contains(msg, banned),
+					"expected error message NOT to contain %q; got %q", banned, msg)
+			}
+			if tc.wantUnwrapsTo != nil {
+				assert.True(t, errors.Is(got, tc.wantUnwrapsTo),
+					"expected wrapped error to unwrap to original via errors.Is")
+			}
+		})
+	}
+}
diff --git a/backend/pkg/providers/providers.go b/backend/pkg/providers/providers.go
index 4e6e49cc..68207afa 100644
--- a/backend/pkg/providers/providers.go
+++ b/backend/pkg/providers/providers.go
@@ -445,7 +445,7 @@ func (pc *providerController) NewFlowProvider(
 
 	tcIDTemplate, err := prv.GetToolCallIDTemplate(ctx, prompter)
 	if err != nil {
-		return nil, fmt.Errorf("failed to determine tool call ID template: %w", err)
+		return nil, wrapToolCallIDTemplateError(err)
 	}
 
 	fp := &flowProvider{
@@ -591,7 +591,7 @@ func (pc *providerController) NewAssistantProvider(
 
 	tcIDTemplate, err := prv.GetToolCallIDTemplate(ctx, prompter)
 	if err != nil {
-		return nil, fmt.Errorf("failed to determine tool call ID template: %w", err)
+		return nil, wrapToolCallIDTemplateError(err)
 	}
 
 	ap := &assistantProvider{