diff --git a/src-docs/src/views/datagrid/schema.js b/src-docs/src/views/datagrid/schema.js
index 91df66542b9..ac6e4997f14 100644
--- a/src-docs/src/views/datagrid/schema.js
+++ b/src-docs/src/views/datagrid/schema.js
@@ -43,21 +43,9 @@ const columns = [
 const data = [];
 
 for (let i = 1; i < 5; i++) {
-  data.push({
-    name: fake('{{name.lastName}}, {{name.firstName}} {{name.suffix}}'),
-    email: <EuiLink href="">{fake('{{internet.email}}')}</EuiLink>,
-    location: (
-      <Fragment>
-        {`${fake('{{address.city}}')}, `}
-        <EuiLink href="https://google.com">
-          {fake('{{address.country}}')}
-        </EuiLink>
-      </Fragment>
-    ),
-    date: fake('{{date.past}}'),
-    account: fake('{{finance.account}}'),
-    amount: fake('${{finance.amount}}'),
-    json: JSON.stringify([
+  let json;
+  if (i < 3) {
+    json = JSON.stringify([
       {
         name: fake('{{name.lastName}}, {{name.firstName}} {{name.suffix}}'),
         email: fake('{{internet.email}}'),
@@ -76,7 +64,30 @@ for (let i = 1; i < 5; i++) {
           },
         ],
       },
-    ]),
+    ]);
+  } else {
+    json = JSON.stringify([
+      {
+        name: fake('{{name.lastName}}, {{name.firstName}} {{name.suffix}}'),
+      },
+    ]);
+  }
+
+  data.push({
+    name: fake('{{name.lastName}}, {{name.firstName}} {{name.suffix}}'),
+    email: <EuiLink href="">{fake('{{internet.email}}')}</EuiLink>,
+    location: (
+      <Fragment>
+        {`${fake('{{address.city}}')}, `}
+        <EuiLink href="https://google.com">
+          {fake('{{address.country}}')}
+        </EuiLink>
+      </Fragment>
+    ),
+    date: fake('{{date.past}}'),
+    account: fake('{{finance.account}}'),
+    amount: fake('${{finance.amount}}'),
+    json: json,
     version: fake('{{system.semver}}'),
   });
 }
diff --git a/src/components/datagrid/column_sorting.tsx b/src/components/datagrid/column_sorting.tsx
index eab6b2bb639..898d00d0128 100644
--- a/src/components/datagrid/column_sorting.tsx
+++ b/src/components/datagrid/column_sorting.tsx
@@ -149,104 +149,110 @@ export const useColumnSorting = (
           </p>
         </EuiText>
       )}
-      <EuiPopoverFooter>
-        <EuiFlexGroup
-          gutterSize="m"
-          justifyContent="spaceBetween"
-          responsive={false}>
-          <EuiFlexItem grow={false}>
-            <EuiPopover
-              data-test-subj="dataGridColumnSortingPopoverColumnSelection"
-              isOpen={avilableColumnsisOpen}
-              closePopover={() => setAvailableColumnsIsOpen(false)}
-              anchorPosition="downLeft"
-              ownFocus
-              panelPaddingSize="s"
-              button={
+      {(inactiveColumns.length > 0 || sorting.columns.length > 0) && (
+        <EuiPopoverFooter>
+          <EuiFlexGroup
+            gutterSize="m"
+            justifyContent="spaceBetween"
+            responsive={false}>
+            <EuiFlexItem grow={false}>
+              {inactiveColumns.length > 0 && (
+                <EuiPopover
+                  data-test-subj="dataGridColumnSortingPopoverColumnSelection"
+                  isOpen={avilableColumnsisOpen}
+                  closePopover={() => setAvailableColumnsIsOpen(false)}
+                  anchorPosition="downLeft"
+                  ownFocus
+                  panelPaddingSize="s"
+                  button={
+                    <EuiButtonEmpty
+                      size="xs"
+                      flush="left"
+                      iconType="arrowDown"
+                      iconSide="right"
+                      onClick={() =>
+                        setAvailableColumnsIsOpen(!avilableColumnsisOpen)
+                      }>
+                      <EuiI18n
+                        token="euiColumnSorting.pickFields"
+                        default="Pick fields to sort by"
+                      />
+                    </EuiButtonEmpty>
+                  }>
+                  <EuiI18n
+                    token="euiColumnSorting.sortFieldAriaLabel"
+                    default="Sort by: ">
+                    {(sortFieldAriaLabel: string) => (
+                      <div
+                        className="euiDataGridColumnSorting__fieldList"
+                        role="listbox">
+                        {inactiveColumns.map(({ id }) => (
+                          <button
+                            key={id}
+                            className="euiDataGridColumnSorting__field"
+                            aria-label={`${sortFieldAriaLabel} ${id}`}
+                            role="option"
+                            aria-selected="false"
+                            data-test-subj={`dataGridColumnSortingPopoverColumnSelection-${id}`}
+                            onClick={() => {
+                              const nextColumns = [...sorting.columns];
+                              nextColumns.push({ id, direction: 'asc' });
+                              sorting.onSort(nextColumns);
+                            }}>
+                            <EuiFlexGroup
+                              alignItems="center"
+                              gutterSize="s"
+                              component="span">
+                              <EuiFlexItem grow={false}>
+                                <EuiIcon
+                                  color={
+                                    schema.hasOwnProperty(id) &&
+                                    schema[id].columnType != null
+                                      ? getDetailsForSchema(
+                                          schema[id].columnType
+                                        ).color
+                                      : defaultSchemaColor
+                                  }
+                                  type={
+                                    schema.hasOwnProperty(id) &&
+                                    schema[id].columnType != null
+                                      ? getDetailsForSchema(
+                                          schema[id].columnType
+                                        ).icon
+                                      : 'string'
+                                  }
+                                />
+                              </EuiFlexItem>
+                              <EuiFlexItem grow={false}>
+                                <EuiText size="xs">
+                                  <span>{id}</span>
+                                </EuiText>
+                              </EuiFlexItem>
+                            </EuiFlexGroup>
+                          </button>
+                        ))}
+                      </div>
+                    )}
+                  </EuiI18n>
+                </EuiPopover>
+              )}
+            </EuiFlexItem>
+            {sorting.columns.length > 0 ? (
+              <EuiFlexItem grow={false}>
                 <EuiButtonEmpty
                   size="xs"
-                  flush="left"
-                  iconType="arrowDown"
-                  iconSide="right"
-                  onClick={() =>
-                    setAvailableColumnsIsOpen(!avilableColumnsisOpen)
-                  }>
+                  flush="right"
+                  onClick={() => sorting.onSort([])}>
                   <EuiI18n
-                    token="euiColumnSorting.pickFields"
-                    default="Pick fields to sort by"
+                    token="euiColumnSorting.clearAll"
+                    default="Clear sorting"
                   />
                 </EuiButtonEmpty>
-              }>
-              <EuiI18n
-                token="euiColumnSorting.sortFieldAriaLabel"
-                default="Sort by: ">
-                {(sortFieldAriaLabel: string) => (
-                  <div
-                    className="euiDataGridColumnSorting__fieldList"
-                    role="listbox">
-                    {inactiveColumns.map(({ id }) => (
-                      <button
-                        key={id}
-                        className="euiDataGridColumnSorting__field"
-                        aria-label={`${sortFieldAriaLabel} ${id}`}
-                        role="option"
-                        aria-selected="false"
-                        data-test-subj={`dataGridColumnSortingPopoverColumnSelection-${id}`}
-                        onClick={() => {
-                          const nextColumns = [...sorting.columns];
-                          nextColumns.push({ id, direction: 'asc' });
-                          sorting.onSort(nextColumns);
-                        }}>
-                        <EuiFlexGroup
-                          alignItems="center"
-                          gutterSize="s"
-                          component="span">
-                          <EuiFlexItem grow={false}>
-                            <EuiIcon
-                              color={
-                                schema.hasOwnProperty(id) &&
-                                schema[id].columnType != null
-                                  ? getDetailsForSchema(schema[id].columnType)
-                                      .color
-                                  : defaultSchemaColor
-                              }
-                              type={
-                                schema.hasOwnProperty(id) &&
-                                schema[id].columnType != null
-                                  ? getDetailsForSchema(schema[id].columnType)
-                                      .icon
-                                  : 'string'
-                              }
-                            />
-                          </EuiFlexItem>
-                          <EuiFlexItem grow={false}>
-                            <EuiText size="xs">
-                              <span>{id}</span>
-                            </EuiText>
-                          </EuiFlexItem>
-                        </EuiFlexGroup>
-                      </button>
-                    ))}
-                  </div>
-                )}
-              </EuiI18n>
-            </EuiPopover>
-          </EuiFlexItem>
-          {sorting.columns.length > 0 ? (
-            <EuiFlexItem grow={false}>
-              <EuiButtonEmpty
-                size="xs"
-                flush="right"
-                onClick={() => sorting.onSort([])}>
-                <EuiI18n
-                  token="euiColumnSorting.clearAll"
-                  default="Clear sorting"
-                />
-              </EuiButtonEmpty>
-            </EuiFlexItem>
-          ) : null}
-        </EuiFlexGroup>
-      </EuiPopoverFooter>
+              </EuiFlexItem>
+            ) : null}
+          </EuiFlexGroup>
+        </EuiPopoverFooter>
+      )}
     </EuiPopover>
   );
 
diff --git a/src/components/datagrid/data_grid.test.tsx b/src/components/datagrid/data_grid.test.tsx
index aaa5ae5f487..ad6b41027f3 100644
--- a/src/components/datagrid/data_grid.test.tsx
+++ b/src/components/datagrid/data_grid.test.tsx
@@ -116,21 +116,24 @@ function getColumnSortDirection(
     columnSelectionPopover = datagrid.find(
       'EuiPopover[data-test-subj="dataGridColumnSortingPopoverColumnSelection"]'
     );
-    expect(columnSelectionPopover).euiPopoverToBeOpen();
+    // popover will go away if all of the columns are selected
+    if (columnSelectionPopover.length > 0) {
+      expect(columnSelectionPopover).euiPopoverToBeOpen();
+
+      popoverButton = columnSelectionPopover
+        .find('div[className="euiPopover__anchor"]')
+        .find('[onClick]')
+        .first();
+      // @ts-ignore-next-line
+      act(() => popoverButton.props().onClick());
 
-    popoverButton = columnSelectionPopover
-      .find('div[className="euiPopover__anchor"]')
-      .find('[onClick]')
-      .first();
-    // @ts-ignore-next-line
-    act(() => popoverButton.props().onClick());
+      datagrid.update();
 
-    datagrid.update();
-
-    columnSelectionPopover = datagrid.find(
-      'EuiPopover[data-test-subj="dataGridColumnSortingPopoverColumnSelection"]'
-    );
-    expect(columnSelectionPopover).not.euiPopoverToBeOpen();
+      columnSelectionPopover = datagrid.find(
+        'EuiPopover[data-test-subj="dataGridColumnSortingPopoverColumnSelection"]'
+      );
+      expect(columnSelectionPopover).not.euiPopoverToBeOpen();
+    }
 
     // find the column sorter
     columnSelectionPopover = datagrid.find(
@@ -1234,6 +1237,34 @@ Array [
         ]);
       });
     });
+
+    it('uses schema information to sort', () => {
+      const component = mount(
+        <EuiDataGrid
+          aria-label="test"
+          columns={[{ id: 'A' }, { id: 'B' }]}
+          rowCount={5}
+          renderCellValue={({ rowIndex, columnId }) =>
+            // render A 0->4 and B 12->8
+            columnId === 'A' ? rowIndex : 12 - rowIndex
+          }
+          inMemory={{ level: 'sorting' }}
+          sorting={{
+            columns: [{ id: 'B', direction: 'asc' }],
+            onSort: () => {},
+          }}
+        />
+      );
+
+      expect(extractGridData(component)).toEqual([
+        ['A', 'B'],
+        ['4', '8'],
+        ['3', '9'],
+        ['2', '10'],
+        ['1', '11'],
+        ['0', '12'],
+      ]);
+    });
   });
 
   describe('keyboard controls', () => {
diff --git a/src/components/datagrid/data_grid.tsx b/src/components/datagrid/data_grid.tsx
index a41283c2dde..b90d15368a0 100644
--- a/src/components/datagrid/data_grid.tsx
+++ b/src/components/datagrid/data_grid.tsx
@@ -7,6 +7,7 @@ import React, {
   useEffect,
   Fragment,
   ReactChild,
+  useMemo,
 } from 'react';
 import classNames from 'classnames';
 import { EuiI18n } from '../i18n';
@@ -44,6 +45,7 @@ import {
   getMergedSchema,
   SchemaDetector,
   useDetectSchema,
+  schemaDetectors as providedSchemaDetectors,
 } from './data_grid_schema';
 import { useColumnSorting } from './column_sorting';
 
@@ -317,9 +319,13 @@ export const EuiDataGrid: FunctionComponent<EuiDataGridProps> = props => {
 
   const [inMemoryValues, onCellRender] = useInMemoryValues(inMemory, rowCount);
 
+  const allSchemaDetetors = useMemo(
+    () => [...providedSchemaDetectors, ...(schemaDetectors || [])],
+    [schemaDetectors]
+  );
   const detectedSchema = useDetectSchema(
     inMemoryValues,
-    schemaDetectors,
+    allSchemaDetetors,
     inMemory != null
   );
   const mergedSchema = getMergedSchema(detectedSchema, columns);
@@ -465,6 +471,7 @@ export const EuiDataGrid: FunctionComponent<EuiDataGridProps> = props => {
                     inMemory={inMemory}
                     columns={visibleColumns}
                     schema={mergedSchema}
+                    schemaDetectors={allSchemaDetetors}
                     expansionFormatters={expansionFormatters}
                     focusedCell={focusedCell}
                     onCellFocus={setFocusedCell}
diff --git a/src/components/datagrid/data_grid_body.tsx b/src/components/datagrid/data_grid_body.tsx
index c081658dbc0..9881a09bf3d 100644
--- a/src/components/datagrid/data_grid_body.tsx
+++ b/src/components/datagrid/data_grid_body.tsx
@@ -23,7 +23,7 @@ import {
   EuiDataGridDataRow,
   EuiDataGridDataRowProps,
 } from './data_grid_data_row';
-import { EuiDataGridSchema } from './data_grid_schema';
+import { EuiDataGridSchema, SchemaDetector } from './data_grid_schema';
 import { useInnerText } from '../inner_text';
 
 interface EuiDataGridBodyProps {
@@ -31,6 +31,7 @@ interface EuiDataGridBodyProps {
   defaultColumnWidth?: number | null;
   columns: EuiDataGridColumn[];
   schema: EuiDataGridSchema;
+  schemaDetectors: SchemaDetector[];
   expansionFormatters?: EuiDataGridExpansionFormatters;
   focusedCell: EuiDataGridDataRowProps['focusedCell'];
   onCellFocus: EuiDataGridDataRowProps['onCellFocus'];
@@ -43,6 +44,16 @@ interface EuiDataGridBodyProps {
   sorting?: EuiDataGridSorting;
 }
 
+const defaultComparator: NonNullable<SchemaDetector['comparator']> = (
+  a,
+  b,
+  direction
+) => {
+  if (a < b) return direction === 'asc' ? -1 : 1;
+  if (a > b) return direction === 'asc' ? 1 : -1;
+  return 0;
+};
+
 const providedExpansionFormatters: EuiDataGridExpansionFormatters = {
   json: ({ children }) => {
     const invisibleRef = useRef<HTMLDivElement>(null);
@@ -102,6 +113,7 @@ export const EuiDataGridBody: FunctionComponent<
     defaultColumnWidth,
     columns,
     schema,
+    schemaDetectors,
     expansionFormatters,
     focusedCell,
     onCellFocus,
@@ -153,8 +165,24 @@ export const EuiDataGridBody: FunctionComponent<
           const aValue = a.values[column.id];
           const bValue = b.values[column.id];
 
-          if (aValue < bValue) return column.direction === 'asc' ? -1 : 1;
-          if (aValue > bValue) return column.direction === 'asc' ? 1 : -1;
+          // get the comparator, based on schema
+          let comparator = defaultComparator;
+          if (schema.hasOwnProperty(column.id)) {
+            const columnType = schema[column.id].columnType;
+            for (let i = 0; i < schemaDetectors.length; i++) {
+              const detector = schemaDetectors[i];
+              if (
+                detector.type === columnType &&
+                detector.hasOwnProperty('comparator')
+              ) {
+                comparator = detector.comparator!;
+              }
+            }
+          }
+
+          const result = comparator(aValue, bValue, column.direction);
+          // only return if the columns are inequal, otherwise allow the next sort-by column to run
+          if (result !== 0) return result;
         }
 
         return 0;
@@ -166,7 +194,7 @@ export const EuiDataGridBody: FunctionComponent<
     }
 
     return rowMap;
-  }, [sorting, inMemory, inMemoryValues]);
+  }, [sorting, inMemory, inMemoryValues, schema, schemaDetectors]);
 
   const setCellFocus = useCallback(
     ([colIndex, rowIndex]) => {
diff --git a/src/components/datagrid/data_grid_schema.tsx b/src/components/datagrid/data_grid_schema.tsx
index a9ad43f2e15..43d0673475e 100644
--- a/src/components/datagrid/data_grid_schema.tsx
+++ b/src/components/datagrid/data_grid_schema.tsx
@@ -11,40 +11,64 @@ import { palettes } from '../../services/color/eui_palettes';
 export interface SchemaDetector {
   type: string;
   detector: (value: string) => number;
+  comparator?: (a: string, b: string, direction: 'asc' | 'desc') => -1 | 0 | 1;
   icon: string;
   color: string;
   sortTextAsc: ReactNode;
   sortTextDesc: ReactNode;
 }
 
-const schemaDetectors: SchemaDetector[] = [
+const numericChars = new Set([
+  '0',
+  '1',
+  '2',
+  '3',
+  '4',
+  '5',
+  '6',
+  '7',
+  '8',
+  '9',
+  '.',
+  '-',
+]);
+export const schemaDetectors: SchemaDetector[] = [
   {
     type: 'boolean',
-    detector(value: string) {
-      return value === 'true' || value === 'false' ? 1 : 0;
+    detector(value) {
+      return value.toLowerCase() === 'true' || value.toLowerCase() === 'false'
+        ? 1
+        : 0;
+    },
+    comparator(a, b, direction) {
+      const aValue = a.toLowerCase() === 'true';
+      const bValue = b.toLowerCase() === 'true';
+      if (aValue < bValue) return direction === 'asc' ? 1 : -1;
+      if (aValue > bValue) return direction === 'asc' ? -1 : 1;
+      return 0;
     },
     icon: 'invert',
     color: palettes.euiPaletteColorBlind.colors[5],
     sortTextAsc: (
       <EuiI18n
         token="euiDataGridSchema.booleanSortTextAsc"
-        default="False-True"
+        default="True-False"
       />
     ),
     sortTextDesc: (
       <EuiI18n
         token="euiDataGridSchema.booleanSortTextDesc"
-        default="True-False"
+        default="False-True"
       />
     ),
   },
   {
     type: 'currency',
-    detector(value: string) {
+    detector(value) {
       const matchLength = (value.match(
         // currency prefers starting with 1-3 characters for the currency symbol
         // then it matches against numerical data + $
-        /(^[^-(]{1,3})?[$-(]*[\d,]+(\.\d*)?[$)]*/
+        /(^[^-(.]{1,3})?[$-(]*[\d,]+(\.\d*)?[$)]*/
       ) || [''])[0].length;
 
       // if there is no currency symbol then reduce the score
@@ -53,6 +77,17 @@ const schemaDetectors: SchemaDetector[] = [
 
       return (matchLength / value.length) * confidenceAdjustment || 0;
     },
+    comparator: (a, b, direction) => {
+      const aChars = a.split('').filter(char => numericChars.has(char));
+      const aValue = parseFloat(aChars.join(''));
+
+      const bChars = b.split('').filter(char => numericChars.has(char));
+      const bValue = parseFloat(bChars.join(''));
+
+      if (aValue < bValue) return direction === 'asc' ? -1 : 1;
+      if (aValue > bValue) return direction === 'asc' ? 1 : -1;
+      return 0;
+    },
     icon: 'currency',
     color: palettes.euiPaletteColorBlind.colors[0],
     sortTextAsc: (
@@ -70,7 +105,7 @@ const schemaDetectors: SchemaDetector[] = [
   },
   {
     type: 'datetime',
-    detector(value: string) {
+    detector(value) {
       // matches the most common forms of ISO-8601
       const isoTimestampMatch = value.match(
         // 2019 - 09    - 17     T 12     : 18    : 32      .853     Z or -0600
@@ -103,11 +138,22 @@ const schemaDetectors: SchemaDetector[] = [
   },
   {
     type: 'numeric',
-    detector(value: string) {
+    detector(value) {
       const matchLength = (value.match(/[%-(]*[\d,]+(\.\d*)?[%)]*/) || [''])[0]
         .length;
       return matchLength / value.length || 0;
     },
+    comparator: (a, b, direction) => {
+      const aChars = a.split('').filter(char => numericChars.has(char));
+      const aValue = parseFloat(aChars.join(''));
+
+      const bChars = b.split('').filter(char => numericChars.has(char));
+      const bValue = parseFloat(bChars.join(''));
+
+      if (aValue < bValue) return direction === 'asc' ? -1 : 1;
+      if (aValue > bValue) return direction === 'asc' ? 1 : -1;
+      return 0;
+    },
     icon: 'number',
     color: palettes.euiPaletteColorBlind.colors[0],
     sortTextAsc: (
@@ -135,6 +181,11 @@ const schemaDetectors: SchemaDetector[] = [
         return 0;
       }
     },
+    comparator: (a, b, direction) => {
+      if (a.length > b.length) return direction === 'asc' ? 1 : -1;
+      if (a.length < b.length) return direction === 'asc' ? 1 : -1;
+      return 0;
+    },
     icon: 'visVega',
     color: palettes.euiPaletteColorBlind.colors[3],
     sortTextAsc: (
@@ -163,13 +214,12 @@ interface SchemaTypeScore {
 
 function scoreValueBySchemaType(
   value: string,
-  extraSchemaDetectors: SchemaDetector[] = []
+  schemaDetectors: SchemaDetector[] = []
 ) {
   const scores: SchemaTypeScore[] = [];
-  const detectors = [...schemaDetectors, ...extraSchemaDetectors];
 
-  for (let i = 0; i < detectors.length; i++) {
-    const { type, detector } = detectors[i];
+  for (let i = 0; i < schemaDetectors.length; i++) {
+    const { type, detector } = schemaDetectors[i];
     const score = detector(value);
     scores.push({ type, score });
   }
@@ -286,7 +336,7 @@ export function useDetectSchema(
       },
       {}
     );
-  }, [inMemoryValues]);
+  }, [inMemoryValues, schemaDetectors]);
   return schema;
 }
 
@@ -294,20 +344,22 @@ export function getMergedSchema(
   detectedSchema: EuiDataGridSchema,
   columns: EuiDataGridColumn[]
 ) {
-  const mergedSchema = { ...detectedSchema };
-
-  for (let i = 0; i < columns.length; i++) {
-    const { id, dataType } = columns[i];
-    if (dataType != null) {
-      if (detectedSchema.hasOwnProperty(id)) {
-        mergedSchema[id] = { ...detectedSchema[id], columnType: dataType };
-      } else {
-        mergedSchema[id] = { columnType: dataType };
+  return useMemo(() => {
+    const mergedSchema = { ...detectedSchema };
+
+    for (let i = 0; i < columns.length; i++) {
+      const { id, dataType } = columns[i];
+      if (dataType != null) {
+        if (detectedSchema.hasOwnProperty(id)) {
+          mergedSchema[id] = { ...detectedSchema[id], columnType: dataType };
+        } else {
+          mergedSchema[id] = { columnType: dataType };
+        }
       }
     }
-  }
 
-  return mergedSchema;
+    return mergedSchema;
+  }, [detectedSchema, columns]);
 }
 
 // Given a provided schema, return the details for the schema