diff --git a/src/components/markdown_editor/__snapshots__/markdown_editor.test.tsx.snap b/src/components/markdown_editor/__snapshots__/markdown_editor.test.tsx.snap
index 5c1842a7c09..20cafbacfc1 100644
--- a/src/components/markdown_editor/__snapshots__/markdown_editor.test.tsx.snap
+++ b/src/components/markdown_editor/__snapshots__/markdown_editor.test.tsx.snap
@@ -153,35 +153,39 @@ exports[`EuiMarkdownEditor is rendered 1`] = `
     </div>
   </div>
   <div
-    class="euiMarkdownEditor__dropZone"
+    style="display:block"
   >
-    <textarea
-      class="euiMarkdownEditor__textArea"
-      id="editorId"
-      rows="6"
-      style="height:calc(118px"
-    />
-    <button
-      class="euiMarkdownEditor__dropZone__button"
+    <div
+      class="euiMarkdownEditor__dropZone"
     >
-      <div
-        aria-hidden="true"
-        class="euiMarkdownEditor__dropZone__icon"
-        data-euiicon-type="paperClip"
+      <textarea
+        class="euiMarkdownEditor__textArea"
+        id="editorId"
+        rows="6"
+        style="height:calc(118px"
       />
-      <div
-        class="euiMarkdownEditor__dropZone__text"
+      <button
+        class="euiMarkdownEditor__dropZone__button"
       >
-        Attach files by dragging & dropping or by clicking this area
-      </div>
-    </button>
-    <input
-      autocomplete="off"
-      multiple=""
-      style="display:none"
-      tabindex="-1"
-      type="file"
-    />
+        <div
+          aria-hidden="true"
+          class="euiMarkdownEditor__dropZone__icon"
+          data-euiicon-type="paperClip"
+        />
+        <div
+          class="euiMarkdownEditor__dropZone__text"
+        >
+          Attach files by dragging & dropping or by clicking this area
+        </div>
+      </button>
+      <input
+        autocomplete="off"
+        multiple=""
+        style="display:none"
+        tabindex="-1"
+        type="file"
+      />
+    </div>
   </div>
 </div>
 `;
diff --git a/src/components/markdown_editor/markdown_actions.ts b/src/components/markdown_editor/markdown_actions.ts
index fac99205526..8c12248a464 100644
--- a/src/components/markdown_editor/markdown_actions.ts
+++ b/src/components/markdown_editor/markdown_actions.ts
@@ -227,14 +227,8 @@ function wordSelectionEnd(text: string, i: number, multiline: boolean): number {
   return index;
 }
 
-let canInsertText: boolean | null = null;
-
-/**
- * Note that we're using the native HTMLTextAreaElement.set() method to play nicely with
- * React's synthetic event system. We fallback to a brute force way of doing it if the
- * above doesn't work. Although all modern browsers, including IE, seem to be fine:
- * https://hustle.bizongo.in/simulate-react-on-change-on-controlled-components-baa336920e04
- */
+const MAX_TRIES = 10;
+const TRY_TIMEOUT = 10 /*ms*/;
 export function insertText(
   textarea: HTMLTextAreaElement,
   { text, selectionStart, selectionEnd }: SelectionRange
@@ -242,39 +236,54 @@ export function insertText(
   const originalSelectionStart = textarea.selectionStart;
   const before = textarea.value.slice(0, originalSelectionStart);
   const after = textarea.value.slice(textarea.selectionEnd);
-  const inputEvent = new Event('input', { bubbles: true });
-
-  if (canInsertText === null || canInsertText === true) {
-    canInsertText = true;
 
-    const nativeInputValueSetter =
-      // @ts-ignore
-      Object.getOwnPropertyDescriptor(
+  // configuration modal/dialog will continue intercepting focus in Safari
+  // need to wait until the textarea can receive focus
+  let tries = 0;
+
+  const insertText = () => {
+    const insertResult = document.execCommand('insertText', false, text);
+
+    if (insertResult === false) {
+      /**
+       * Fallback for Firefox; this kills undo/redo but at least updates the value
+       *
+       * Note that we're using the native HTMLTextAreaElement.set() method to play nicely with
+       * React's synthetic event system.
+       * https://hustle.bizongo.in/simulate-react-on-change-on-controlled-components-baa336920e04
+       */
+      const inputEvent = new Event('input', { bubbles: true });
+      const nativeInputValueSetter =
         // @ts-ignore
-        window.HTMLTextAreaElement.prototype,
-        'value'
-      ).set;
-    try {
+        Object.getOwnPropertyDescriptor(
+          // @ts-ignore
+          window.HTMLTextAreaElement.prototype,
+          'value'
+        ).set;
       // @ts-ignore
       nativeInputValueSetter.call(textarea, before + text + after);
-
       textarea.dispatchEvent(inputEvent);
-    } catch (error) {
-      canInsertText = false;
     }
-  }
 
-  if (!canInsertText) {
-    // If calling [HTMLTextAreaElement.set()] fails, just brute-force it
-    textarea.value = before + text + after;
-    textarea.dispatchEvent(inputEvent);
-  }
+    if (selectionStart != null && selectionEnd != null) {
+      textarea.setSelectionRange(selectionStart, selectionEnd);
+    } else {
+      textarea.setSelectionRange(originalSelectionStart, textarea.selectionEnd);
+    }
+  };
+
+  const focusTextarea = () => {
+    textarea.focus();
+    if (document.activeElement === textarea) {
+      insertText();
+    } else if (++tries === MAX_TRIES) {
+      insertText();
+    } else {
+      setTimeout(focusTextarea, TRY_TIMEOUT);
+    }
+  };
 
-  if (selectionStart != null && selectionEnd != null) {
-    textarea.setSelectionRange(selectionStart, selectionEnd);
-  } else {
-    textarea.setSelectionRange(originalSelectionStart, textarea.selectionEnd);
-  }
+  focusTextarea();
 }
 
 function styleSelectedText(
diff --git a/src/components/markdown_editor/markdown_editor.tsx b/src/components/markdown_editor/markdown_editor.tsx
index 7230e039ccd..3bcde41413d 100644
--- a/src/components/markdown_editor/markdown_editor.tsx
+++ b/src/components/markdown_editor/markdown_editor.tsx
@@ -228,56 +228,56 @@ export const EuiMarkdownEditor: FunctionComponent<EuiMarkdownEditorProps> = ({
           uiPlugins={uiPlugins}
         />
 
-        {isPreviewing ? (
+        {isPreviewing && (
           <div
             className="euiMarkdownEditor__preview"
             style={{ height: `${height}px` }}>
             <EuiMarkdownFormat processor={processor}>{value}</EuiMarkdownFormat>
           </div>
-        ) : (
-          <>
-            <EuiMarkdownEditorDropZone>
-              <EuiMarkdownEditorTextArea
-                ref={setTextareaRef}
-                height={height}
-                id={editorId}
-                onChange={e => onChange(e.target.value)}
-                value={value}
-              />
-            </EuiMarkdownEditorDropZone>
-            {textareaRef && pluginEditorPlugin && (
-              <EuiOverlayMask>
-                <EuiModal onClose={() => setPluginEditorPlugin(undefined)}>
-                  {createElement(pluginEditorPlugin.editor!, {
-                    node:
+        )}
+        {/* Toggle the editor's display instead of unmounting to retain its undo/redo history */}
+        <div style={{ display: isPreviewing ? 'none' : 'block' }}>
+          <EuiMarkdownEditorDropZone>
+            <EuiMarkdownEditorTextArea
+              ref={setTextareaRef}
+              height={height}
+              id={editorId}
+              onChange={e => onChange(e.target.value)}
+              value={value}
+            />
+          </EuiMarkdownEditorDropZone>
+          {textareaRef && pluginEditorPlugin && (
+            <EuiOverlayMask>
+              <EuiModal onClose={() => setPluginEditorPlugin(undefined)}>
+                {createElement(pluginEditorPlugin.editor!, {
+                  node:
+                    selectedNode &&
+                    selectedNode.type === pluginEditorPlugin.name
+                      ? selectedNode
+                      : null,
+                  onCancel: () => setPluginEditorPlugin(undefined),
+                  onSave: markdown => {
+                    if (
                       selectedNode &&
                       selectedNode.type === pluginEditorPlugin.name
-                        ? selectedNode
-                        : null,
-                    onCancel: () => setPluginEditorPlugin(undefined),
-                    onSave: markdown => {
-                      if (
-                        selectedNode &&
-                        selectedNode.type === pluginEditorPlugin.name
-                      ) {
-                        textareaRef.setSelectionRange(
-                          selectedNode.position.start.offset,
-                          selectedNode.position.end.offset
-                        );
-                      }
-                      insertText(textareaRef, {
-                        text: markdown,
-                        selectionStart: undefined,
-                        selectionEnd: undefined,
-                      });
-                      setPluginEditorPlugin(undefined);
-                    },
-                  })}
-                </EuiModal>
-              </EuiOverlayMask>
-            )}
-          </>
-        )}
+                    ) {
+                      textareaRef.setSelectionRange(
+                        selectedNode.position.start.offset,
+                        selectedNode.position.end.offset
+                      );
+                    }
+                    insertText(textareaRef, {
+                      text: markdown,
+                      selectionStart: undefined,
+                      selectionEnd: undefined,
+                    });
+                    setPluginEditorPlugin(undefined);
+                  },
+                })}
+              </EuiModal>
+            </EuiOverlayMask>
+          )}
+        </div>
       </div>
     </EuiMarkdownContext.Provider>
   );