diff --git a/application/ui/src/features/annotator/tools/tools.component.tsx b/application/ui/src/features/annotator/tools/tools.component.tsx
index 781873fe53..63acc246d8 100644
--- a/application/ui/src/features/annotator/tools/tools.component.tsx
+++ b/application/ui/src/features/annotator/tools/tools.component.tsx
@@ -1,7 +1,7 @@
 // Copyright (C) 2025 Intel Corporation
 // SPDX-License-Identifier: Apache-2.0
 
-import { ActionButton } from '@geti/ui';
+import { ActionButton, Tooltip, TooltipTrigger } from '@geti/ui';
 import { useHotkeys } from 'react-hotkeys-hook';
 import { Fragment } from 'react/jsx-runtime';
 
@@ -18,16 +18,21 @@ const Tool = ({ tool, activeTool, setActiveTool }: ToolProps) => {
     useHotkeys(tool.hotkey, () => setActiveTool(tool.type), [setActiveTool]);
 
     return (
-        <ActionButton
-            isQuiet
-            width={'size-400'}
-            onPress={() => setActiveTool(tool.type)}
-            aria-label={`${tool.type} tool`}
-        >
-            <IconWrapper isSelected={activeTool === tool.type}>
-                <tool.icon data-tool={tool.type} />
-            </IconWrapper>
-        </ActionButton>
+        <TooltipTrigger placement={'right'}>
+            <ActionButton
+                isQuiet
+                width={'size-400'}
+                onPress={() => setActiveTool(tool.type)}
+                aria-label={`${tool.type} tool`}
+            >
+                <IconWrapper isSelected={activeTool === tool.type}>
+                    <tool.icon data-tool={tool.type} />
+                </IconWrapper>
+            </ActionButton>
+            <Tooltip>
+                {tool.label} ({tool.hotkey})
+            </Tooltip>
+        </TooltipTrigger>
     );
 };
 
diff --git a/application/ui/src/features/dataset/media-preview/primary-toolbar/toggle-annotations-visibility.component.tsx b/application/ui/src/features/dataset/media-preview/primary-toolbar/toggle-annotations-visibility.component.tsx
index 9e6b50140c..f9865b637d 100644
--- a/application/ui/src/features/dataset/media-preview/primary-toolbar/toggle-annotations-visibility.component.tsx
+++ b/application/ui/src/features/dataset/media-preview/primary-toolbar/toggle-annotations-visibility.component.tsx
@@ -14,7 +14,7 @@ export const ToggleAnnotationsVisibility = () => {
     useHotkeys(HOTKEYS.toggleAnnotationsVisibility, toggleVisibility, [toggleVisibility]);
 
     return (
-        <TooltipTrigger>
+        <TooltipTrigger placement={'right'}>
             <ActionButton aria-label={`${isVisible ? 'Hide' : 'Show'} annotations`} isQuiet onPress={toggleVisibility}>
                 {isVisible ? <Visible /> : <Invisible />}
             </ActionButton>
diff --git a/application/ui/src/features/models/train-model/select-dataset-revision.component.tsx b/application/ui/src/features/models/train-model/select-dataset-revision.component.tsx
index 888925c872..111e6d3700 100644
--- a/application/ui/src/features/models/train-model/select-dataset-revision.component.tsx
+++ b/application/ui/src/features/models/train-model/select-dataset-revision.component.tsx
@@ -1,7 +1,7 @@
 // Copyright (C) 2025 Intel Corporation
 // SPDX-License-Identifier: Apache-2.0
 
-import { Item, Picker } from '@geti/ui';
+import { Content, ContextualHelp, Heading, Item, Picker } from '@geti/ui';
 
 import { useTrainModel } from './train-model-provider.component';
 
@@ -9,14 +9,28 @@ export const SelectDatasetRevision = () => {
     const { datasetRevisions, selectedDatasetRevisionId, onSelectDatasetRevisionId } = useTrainModel();
 
     return (
-        <Picker
-            flex={1}
-            items={datasetRevisions}
-            label={'Select dataset revision'}
-            selectedKey={selectedDatasetRevisionId}
-            onSelectionChange={(key) => onSelectDatasetRevisionId(String(key))}
-        >
-            {(item) => <Item key={item.id}>{item.name}</Item>}
-        </Picker>
+        <>
+            <Picker
+                flex={1}
+                items={datasetRevisions}
+                label={'Select dataset'}
+                selectedKey={selectedDatasetRevisionId}
+                onSelectionChange={(key) => onSelectDatasetRevisionId(String(key))}
+                contextualHelp={
+                    <ContextualHelp variant={'info'} placement={'top'}>
+                        <Heading>Selecting a dataset</Heading>
+                        <Content>
+                            {`Choose the version of the dataset to use for training. If you want to train the new model 
+                            on the exact same data (media and annotations) as another model, please select the
+                            corresponding dataset revision. Conversely, if you want to train on the most recent version
+                            of the data (what you see in the "Dataset" page), please select "Use
+                            current dataset".`}
+                        </Content>
+                    </ContextualHelp>
+                }
+            >
+                {(item) => <Item key={item.id}>{item.name}</Item>}
+            </Picker>
+        </>
     );
 };
diff --git a/application/ui/src/features/models/train-model/train-model-dialog.component.tsx b/application/ui/src/features/models/train-model/train-model-dialog.component.tsx
index 3bde19fb7a..65fea78021 100644
--- a/application/ui/src/features/models/train-model/train-model-dialog.component.tsx
+++ b/application/ui/src/features/models/train-model/train-model-dialog.component.tsx
@@ -1,12 +1,26 @@
 // Copyright (C) 2025 Intel Corporation
 // SPDX-License-Identifier: Apache-2.0
 
-import { Button, ButtonGroup, Content, Dialog, Divider, Flex, Heading, Link, Text, toast } from '@geti/ui';
+import {
+    Button,
+    ButtonGroup,
+    Content,
+    Dialog,
+    Divider,
+    Flex,
+    Footer,
+    Heading,
+    InlineAlert,
+    Link,
+    Text,
+    toast,
+} from '@geti/ui';
 import { useProjectIdentifier } from 'hooks/use-project-identifier.hook';
 import { useMatch } from 'react-router';
 
 import { paths } from '../../../constants/paths';
 import { useTrainModelMutation } from '../hooks/api/use-train-model-mutation';
+import { useIsTrainingButtonDisabled } from '../hooks/use-is-training-button-disabled';
 import { TrainModelDialogContent } from './train-model-dialog-content';
 import { useTrainModel } from './train-model-provider.component';
 
@@ -20,8 +34,10 @@ export const TrainModelDialog = ({ onClose }: TrainModelDialogProps) => {
     const trainModelMutation = useTrainModelMutation();
     const projectId = useProjectIdentifier();
     const isModelsPage = useMatch(paths.project.models.pattern);
+    const isTrainingDisabled = useIsTrainingButtonDisabled();
 
-    const isStartButtonDisabled = selectedModelArchitectureId === null || selectedTrainingDevice === null;
+    const isStartButtonDisabled =
+        isTrainingDisabled || selectedModelArchitectureId === null || selectedTrainingDevice === null;
 
     const trainModel = () => {
         if (isStartButtonDisabled) return;
@@ -57,21 +73,39 @@ export const TrainModelDialog = ({ onClose }: TrainModelDialogProps) => {
     };
 
     return (
-        <Dialog width={'clamp(800px, 50vw, 1150px'}>
+        <Dialog width={'clamp(800px, 50vw, 1150px)'}>
             <Heading>Select a model to train</Heading>
+
             <Divider size={'S'} />
+
             <Content>
                 <TrainModelDialogContent />
             </Content>
+
             <Divider size={'S'} />
-            <ButtonGroup>
-                <Button variant={'secondary'} onPress={onClose}>
-                    Cancel
-                </Button>
-                <Button variant={'accent'} onPress={trainModel} isDisabled={isStartButtonDisabled}>
-                    Start
-                </Button>
-            </ButtonGroup>
+
+            <Footer>
+                <Flex alignItems={'center'} marginBottom={'size-200'}>
+                    {isTrainingDisabled ? (
+                        <InlineAlert variant={'notice'}>
+                            <Heading>Why can I not start training?</Heading>
+                            <Content>
+                                In order to train a model, you need to annotate at least 3 items in your dataset,
+                                although we recommend annotating at least 10 for better results.
+                            </Content>
+                        </InlineAlert>
+                    ) : null}
+                </Flex>
+
+                <ButtonGroup marginStart={'auto'}>
+                    <Button variant={'secondary'} onPress={onClose}>
+                        Cancel
+                    </Button>
+                    <Button variant={'accent'} onPress={trainModel} isDisabled={isStartButtonDisabled}>
+                        Start
+                    </Button>
+                </ButtonGroup>
+            </Footer>
         </Dialog>
     );
 };
diff --git a/application/ui/src/features/models/train-model/train-model-provider.component.tsx b/application/ui/src/features/models/train-model/train-model-provider.component.tsx
index bf204c05fe..34fb07c064 100644
--- a/application/ui/src/features/models/train-model/train-model-provider.component.tsx
+++ b/application/ui/src/features/models/train-model/train-model-provider.component.tsx
@@ -44,7 +44,7 @@ const useDatasetRevisions = () => {
     const { data: datasetRevisions } = useGetDatasetRevisions();
     return {
         datasetRevisions: [
-            { id: 'use-current-dataset-revision', name: 'Use current revision', value: null },
+            { id: 'use-current-dataset-revision', name: 'Use current dataset', value: null },
             ...(datasetRevisions?.map(({ id, name }) => ({ id, name, value: String(id) })) ?? []),
         ],
     };
diff --git a/application/ui/src/features/models/train-model/train-model.test.tsx b/application/ui/src/features/models/train-model/train-model.component.test.tsx
similarity index 54%
rename from application/ui/src/features/models/train-model/train-model.test.tsx
rename to application/ui/src/features/models/train-model/train-model.component.test.tsx
index 101933325b..3ee581b8ea 100644
--- a/application/ui/src/features/models/train-model/train-model.test.tsx
+++ b/application/ui/src/features/models/train-model/train-model.component.test.tsx
@@ -1,7 +1,9 @@
 // Copyright (C) 2025-2026 Intel Corporation
 // SPDX-License-Identifier: Apache-2.0
 
-import { screen, waitFor } from '@testing-library/react';
+import { fireEvent, screen, waitFor } from '@testing-library/react';
+import { getMockedPipeline } from 'mocks/mock-pipeline';
+import { getMockedProject } from 'mocks/mock-project';
 import { HttpResponse } from 'msw';
 import { render } from 'test-utils/render';
 
@@ -10,7 +12,30 @@ import { server } from '../../../msw-node-setup';
 import { TrainModel } from './train-model.component';
 
 describe('TrainModel', () => {
-    it('disables train model button when there are no enough annotated media items', async () => {
+    beforeEach(() => {
+        server.use(
+            http.get('/api/projects/{project_id}', () => {
+                return HttpResponse.json(getMockedProject({ id: '123' }));
+            }),
+            http.get('/api/projects/{project_id}/pipeline', () => {
+                return HttpResponse.json(getMockedPipeline({}));
+            }),
+            http.get('/api/projects/{project_id}/dataset_revisions', () => {
+                return HttpResponse.json([]);
+            }),
+            http.get('/api/model_architectures', () => {
+                return HttpResponse.json({
+                    model_architectures: [],
+                    top_picks: null,
+                });
+            }),
+            http.get('/api/system/devices/training', () => {
+                return HttpResponse.json([{ type: 'cpu', name: 'CPU' }]);
+            })
+        );
+    });
+
+    it('shows warning message when there are not enough annotated media items', async () => {
         server.use(
             http.get('/api/projects/{project_id}/dataset/items', () => {
                 return HttpResponse.json({
@@ -23,14 +48,10 @@ describe('TrainModel', () => {
                             id: '2',
                             subset: 'unassigned',
                         },
-                        {
-                            id: '3',
-                            subset: 'unassigned',
-                        },
                     ],
                     pagination: {
-                        total: 3,
-                        count: 3,
+                        total: 2,
+                        count: 2,
                         limit: 10,
                         offset: 0,
                     },
@@ -40,12 +61,14 @@ describe('TrainModel', () => {
 
         render(<TrainModel />);
 
-        await waitFor(() => {
-            expect(screen.getByRole('button', { name: 'Train model' })).toBeDisabled();
-        });
+        fireEvent.click(screen.getByRole('button', { name: 'Train model' }));
+
+        expect(
+            await screen.findByText(/In order to train a model, you need to annotate at least 3 items/)
+        ).toBeVisible();
     });
 
-    it('enables train model button when there are enough annotated media items', async () => {
+    it('does not show warning message when there are enough annotated media items', async () => {
         server.use(
             http.get('/api/projects/{project_id}/dataset/items', () => {
                 return HttpResponse.json({
@@ -79,8 +102,12 @@ describe('TrainModel', () => {
 
         render(<TrainModel />);
 
+        fireEvent.click(screen.getByRole('button', { name: 'Train model' }));
+
         await waitFor(() => {
-            expect(screen.getByRole('button', { name: 'Train model' })).toBeEnabled();
+            expect(
+                screen.queryByText(/In order to train a model, you need to annotate at least 3 items/)
+            ).not.toBeInTheDocument();
         });
     });
 });
diff --git a/application/ui/src/features/models/train-model/train-model.component.tsx b/application/ui/src/features/models/train-model/train-model.component.tsx
index 543ad52e34..37e88ca22d 100644
--- a/application/ui/src/features/models/train-model/train-model.component.tsx
+++ b/application/ui/src/features/models/train-model/train-model.component.tsx
@@ -5,7 +5,6 @@ import { Suspense } from 'react';
 
 import { Button, DialogTrigger, Loading, View } from '@geti/ui';
 
-import { useIsTrainingButtonDisabled } from '../hooks/use-is-training-button-disabled';
 import { TrainModelDialog } from './train-model-dialog.component';
 import { TrainModelProvider } from './train-model-provider.component';
 
@@ -14,11 +13,9 @@ type TrainModelProps = {
 };
 
 export const TrainModel = ({ preSelectedDatasetRevisionId }: TrainModelProps) => {
-    const isTrainingDisabled = useIsTrainingButtonDisabled();
-
     return (
         <DialogTrigger>
-            <Button isDisabled={isTrainingDisabled}>Train model</Button>
+            <Button>Train model</Button>
             {(close) => (
                 <Suspense
                     fallback={