diff --git a/client/dist/js/TinyMCE_sslink-anchor.js b/client/dist/js/TinyMCE_sslink-anchor.js
index 112518f5..33ab49bc 100644
--- a/client/dist/js/TinyMCE_sslink-anchor.js
+++ b/client/dist/js/TinyMCE_sslink-anchor.js
@@ -1 +1 @@
-!function(){"use strict";var e={964:function(e,t){Object.defineProperty(t,"__esModule",{value:!0}),t.default=void 0;t.default={ANCHORSELECTOR_CURRENT_FIELD:"ANCHORSELECTOR_CURRENT_FIELD",ANCHORSELECTOR_UPDATED:"ANCHORSELECTOR_UPDATED",ANCHORSELECTOR_UPDATING:"ANCHORSELECTOR_UPDATING",ANCHORSELECTOR_UPDATE_FAILED:"ANCHORSELECTOR_UPDATE_FAILED"}},447:function(e,t,n){Object.defineProperty(t,"__esModule",{value:!0}),t.beginUpdating=function(e){return{type:i.default.ANCHORSELECTOR_UPDATING,payload:{pageId:e}}},t.updateFailed=function(e){return{type:i.default.ANCHORSELECTOR_UPDATE_FAILED,payload:{pageId:e}}},t.updated=function(e,t){let n=arguments.length>2&&void 0!==arguments[2]&&arguments[2];return{type:i.default.ANCHORSELECTOR_UPDATED,payload:{pageId:e,anchors:t,cacheResult:n}}},t.updatedCurrentField=function(e,t,n){return{type:i.default.ANCHORSELECTOR_CURRENT_FIELD,payload:{pageId:e,anchors:t,fieldID:n}}};var r,i=(r=n(964))&&r.__esModule?r:{default:r}},939:function(e){e.exports=ApolloClient},648:function(e){e.exports=Injector},595:function(e){e.exports=InsertLinkModal},363:function(e){e.exports=React},691:function(e){e.exports=ReactDomClient},624:function(e){e.exports=ReactRedux},265:function(e){e.exports=ShortcodeSerialiser},196:function(e){e.exports=TinyMCEActionRegistrar},754:function(e){e.exports=i18n},311:function(e){e.exports=jQuery}},t={};function n(r){var i=t[r];if(void 0!==i)return i.exports;var o=t[r]={exports:{}};return e[r](o,o.exports,n),o.exports}!function(){var e=p(n(754)),t=p(n(196)),r=p(n(363)),i=n(691),o=n(939),a=n(624),d=p(n(311)),l=p(n(265)),s=n(595),u=n(648),c=n(447);function p(e){return e&&e.__esModule?e:{default:e}}const f="sslinkanchor";t.default.addAction("sslink",{text:e.default._t("CMS.LINKLABEL_ANCHOR","Anchor on a page"),onAction:e=>e.execCommand(f),priority:60},editorIdentifier).addCommandWithUrlTest(f,/^\[sitetree_link.+]#[^#\]]+$/);const E={init(e){e.addCommand(f,(()=>{const t=(0,d.default)(`#${e.id}`).entwine("ss"),n=Number((0,d.default)("#Form_EditForm_ID").val()||0),r=(0,d.default)(e.getBody()).find("[id],[name]").toArray().map((e=>e.id||e.name));ss.store.dispatch((0,c.updatedCurrentField)(n,r,e.id)),t.openLinkAnchorDialog()}))}},A="insert-link__dialog-wrapper--anchor",C=(0,u.provideInjector)((0,s.createInsertLinkModal)("SilverStripe\\CMS\\Controllers\\CMSPageEditController","editorAnchorLink"));d.default.entwine("ss",(t=>{t("textarea.htmleditor").entwine({openLinkAnchorDialog(){let e=t(`#${A}`);e.length||(e=t(`<div id="${A}" />`),t("body").append(e)),e.addClass("insert-link__dialog-wrapper"),e.setElement(this),e.open()}}),t(`#${A}`).entwine({ReactRoot:null,renderModal(n){var d=this;const l=ss.store,s=ss.apolloClient,u=this.getOriginalAttributes(),c=this.getElement().getEditor(),p=c.getInstance().selection,f=c.getSelection(),E="A"!==p.getNode().tagName&&""===f.trim(),A=Number(t("#Form_EditForm_ID").val()||0);let _=this.getReactRoot();_||(_=(0,i.createRoot)(this[0]),this.setReactRoot(_)),_.render(r.default.createElement(o.ApolloProvider,{client:s},r.default.createElement(a.Provider,{store:l},r.default.createElement(C,{isOpen:n,onInsert:function(){return d.handleInsert(...arguments)},onClosed:()=>this.close(),title:e.default._t("CMS.LINK_ANCHOR","Link to an anchor on a page"),bodyClassName:"modal__dialog",className:"insert-link__dialog-wrapper--anchor",fileAttributes:u,identifier:"Admin.InsertLinkAnchorModal",requireLinkText:E,currentPageID:A}))))},buildAttributes(e){return{href:`${l.default.serialise({name:"sitetree_link",properties:{id:e.PageID}},!0)}${e.Anchor&&e.Anchor.length?`#${e.Anchor}`:""}`,target:e.TargetBlank?"_blank":"",title:e.Description}},getOriginalAttributes(){const e=this.getElement().getEditor(),n=t(e.getSelectedNode()),r=(n.attr("href")||"").split("#");if(!r[0])return{};const i=l.default.match("sitetree_link",!1,r[0]);return i?{PageID:i.properties.id?parseInt(i.properties.id,10):0,Anchor:r[1]||"",Description:n.attr("title"),TargetBlank:!!n.attr("target")}:{}}})})),tinymce.PluginManager.add(f,(e=>E.init(e)))}()}();
\ No newline at end of file
+!function(){"use strict";var e={964:function(e,t){Object.defineProperty(t,"__esModule",{value:!0}),t.default=void 0;t.default={ANCHORSELECTOR_CURRENT_FIELD:"ANCHORSELECTOR_CURRENT_FIELD",ANCHORSELECTOR_UPDATED:"ANCHORSELECTOR_UPDATED",ANCHORSELECTOR_UPDATING:"ANCHORSELECTOR_UPDATING",ANCHORSELECTOR_UPDATE_FAILED:"ANCHORSELECTOR_UPDATE_FAILED"}},447:function(e,t,n){Object.defineProperty(t,"__esModule",{value:!0}),t.beginUpdating=function(e){return{type:i.default.ANCHORSELECTOR_UPDATING,payload:{pageId:e}}},t.updateFailed=function(e){return{type:i.default.ANCHORSELECTOR_UPDATE_FAILED,payload:{pageId:e}}},t.updated=function(e,t){let n=arguments.length>2&&void 0!==arguments[2]&&arguments[2];return{type:i.default.ANCHORSELECTOR_UPDATED,payload:{pageId:e,anchors:t,cacheResult:n}}},t.updatedCurrentField=function(e,t,n){return{type:i.default.ANCHORSELECTOR_CURRENT_FIELD,payload:{pageId:e,anchors:t,fieldID:n}}};var r,i=(r=n(964))&&r.__esModule?r:{default:r}},939:function(e){e.exports=ApolloClient},648:function(e){e.exports=Injector},595:function(e){e.exports=InsertLinkModal},363:function(e){e.exports=React},691:function(e){e.exports=ReactDomClient},624:function(e){e.exports=ReactRedux},265:function(e){e.exports=ShortcodeSerialiser},196:function(e){e.exports=TinyMCEActionRegistrar},754:function(e){e.exports=i18n},311:function(e){e.exports=jQuery}},t={};function n(r){var i=t[r];if(void 0!==i)return i.exports;var o=t[r]={exports:{}};return e[r](o,o.exports,n),o.exports}!function(){var e=p(n(754)),t=p(n(196)),r=p(n(363)),i=n(691),o=n(939),a=n(624),d=p(n(311)),l=p(n(265)),s=n(595),u=n(648),c=n(447);function p(e){return e&&e.__esModule?e:{default:e}}const f="sslinkanchor";t.default.addAction("sslink",{text:e.default._t("CMS.LINKLABEL_ANCHOR","Anchor on a page"),onAction:e=>e.execCommand(f),priority:60},editorIdentifier).addCommandWithUrlTest(f,/^\[sitetree_link.+]#[^#\]]+$/);const E={init(e){e.addCommand(f,(()=>{const t=(0,d.default)(`#${e.id}`).entwine("ss"),n=Number((0,d.default)("#Form_EditForm_ID").val()||0),r=(0,d.default)(e.getBody()).find("[id],[name]").toArray().map((e=>e.id||e.name));ss.store.dispatch((0,c.updatedCurrentField)(n,r,e.id)),t.openLinkAnchorDialog()}))}},A="insert-link__dialog-wrapper--anchor",C=(0,u.provideInjector)((0,s.createInsertLinkModal)("SilverStripe\\CMS\\Controllers\\CMSPageEditController","editorAnchorLink"));d.default.entwine("ss",(t=>{t("textarea.htmleditor").entwine({openLinkAnchorDialog(){let e=t(`#${A}`);e.length||(e=t(`<div id="${A}" />`),t("body").append(e)),e.addClass("insert-link__dialog-wrapper"),e.setElement(this),e.open()}}),t(`#${A}`).entwine({ReactRoot:null,renderModal(n){var d=this;const l=ss.store,s=ss.apolloClient,u=this.getOriginalAttributes(),c=this.getRequireLinkText(),p=Number(t("#Form_EditForm_ID").val()||0);let f=this.getReactRoot();f||(f=(0,i.createRoot)(this[0]),this.setReactRoot(f)),f.render(r.default.createElement(o.ApolloProvider,{client:s},r.default.createElement(a.Provider,{store:l},r.default.createElement(C,{isOpen:n,onInsert:function(){return d.handleInsert(...arguments)},onClosed:()=>this.close(),title:e.default._t("CMS.LINK_ANCHOR","Link to an anchor on a page"),bodyClassName:"modal__dialog",className:"insert-link__dialog-wrapper--anchor",fileAttributes:u,identifier:"Admin.InsertLinkAnchorModal",requireLinkText:c,currentPageID:p}))))},buildAttributes(e){return{href:`${l.default.serialise({name:"sitetree_link",properties:{id:e.PageID}},!0)}${e.Anchor&&e.Anchor.length?`#${e.Anchor}`:""}`,target:e.TargetBlank?"_blank":"",title:e.Description}},getOriginalAttributes(){const e=this.getElement().getEditor(),n=t(e.getSelectedNode()),r=(n.attr("href")||"").split("#");if(!r[0])return{};const i=l.default.match("sitetree_link",!1,r[0]);return i?{PageID:i.properties.id?parseInt(i.properties.id,10):0,Anchor:r[1]||"",Description:n.attr("title"),TargetBlank:!!n.attr("target")}:{}}})})),tinymce.PluginManager.add(f,(e=>E.init(e)))}()}();
\ No newline at end of file
diff --git a/client/dist/js/TinyMCE_sslink-internal.js b/client/dist/js/TinyMCE_sslink-internal.js
index 75ec192a..b6cfee8c 100644
--- a/client/dist/js/TinyMCE_sslink-internal.js
+++ b/client/dist/js/TinyMCE_sslink-internal.js
@@ -1 +1 @@
-!function(){"use strict";var e={939:function(e){e.exports=ApolloClient},648:function(e){e.exports=Injector},595:function(e){e.exports=InsertLinkModal},363:function(e){e.exports=React},691:function(e){e.exports=ReactDomClient},624:function(e){e.exports=ReactRedux},265:function(e){e.exports=ShortcodeSerialiser},196:function(e){e.exports=TinyMCEActionRegistrar},754:function(e){e.exports=i18n},311:function(e){e.exports=jQuery}},t={};function n(i){var r=t[i];if(void 0!==r)return r.exports;var o=t[i]={exports:{}};return e[i](o,o.exports,n),o.exports}!function(){var e=u(n(754)),t=u(n(196)),i=u(n(363)),r=n(691),o=n(939),a=n(624),l=u(n(311)),s=u(n(265)),d=n(595),c=n(648);function u(e){return e&&e.__esModule?e:{default:e}}const p="sslinkinternal";t.default.addAction("sslink",{text:e.default._t("CMS.LINKLABEL_PAGE","Page on this site"),onAction:e=>e.execCommand(p),priority:90},editorIdentifier).addCommandWithUrlTest(p,/^\[sitetree_link.+]$/);const g={init(e){e.addCommand(p,(()=>{(0,l.default)(`#${e.id}`).entwine("ss").openLinkInternalDialog()}))}},f="insert-link__dialog-wrapper--internal",h=(0,c.provideInjector)((0,d.createInsertLinkModal)("SilverStripe\\CMS\\Controllers\\CMSPageEditController","editorInternalLink"));l.default.entwine("ss",(t=>{t("textarea.htmleditor").entwine({openLinkInternalDialog(){let e=t(`#${f}`);e.length||(e=t(`<div id="${f}" />`),t("body").append(e)),e.addClass("insert-link__dialog-wrapper"),e.setElement(this),e.open()}}),t(`#${f}`).entwine({ReactRoot:null,renderModal(t){var n=this;const l=ss.store,s=ss.apolloClient,d=this.getOriginalAttributes(),c=this.getRequireLinkText();let u=this.getReactRoot();u||(u=(0,r.createRoot)(this[0]),this.setReactRoot(u)),u.render(i.default.createElement(o.ApolloProvider,{client:s},i.default.createElement(a.Provider,{store:l},i.default.createElement(h,{isOpen:t,onInsert:function(){return n.handleInsert(...arguments)},onClosed:()=>this.close(),title:e.default._t("CMS.LINK_PAGE","Link to a page"),bodyClassName:"modal__dialog",className:"insert-link__dialog-wrapper--internal",fileAttributes:d,identifier:"Admin.InsertLinkInternalModal",requireLinkText:c}))))},getRequireLinkText(){const e=this.getElement().getEditor(),t=e.getInstance().selection,n=e.getSelection();return"A"!==t.getNode().tagName&&""===n.trim()},buildAttributes(e){return{href:`${s.default.serialise({name:"sitetree_link",properties:{id:e.PageID}},!0)}${e.Anchor&&e.Anchor.length?`#${e.Anchor}`:""}`,target:e.TargetBlank?"_blank":"",title:e.Description}},getOriginalAttributes(){const e=this.getElement().getEditor(),n=t(e.getSelectedNode()),i=(n.attr("href")||"").split("#");if(!i[0])return{};const r=s.default.match("sitetree_link",!1,i[0]);return r?{PageID:r.properties.id?parseInt(r.properties.id,10):0,Anchor:i[1]||"",Description:n.attr("title"),TargetBlank:!!n.attr("target")}:{}}})})),tinymce.PluginManager.add(p,(e=>g.init(e)))}()}();
\ No newline at end of file
+!function(){"use strict";var e={939:function(e){e.exports=ApolloClient},648:function(e){e.exports=Injector},595:function(e){e.exports=InsertLinkModal},363:function(e){e.exports=React},691:function(e){e.exports=ReactDomClient},624:function(e){e.exports=ReactRedux},265:function(e){e.exports=ShortcodeSerialiser},196:function(e){e.exports=TinyMCEActionRegistrar},754:function(e){e.exports=i18n},311:function(e){e.exports=jQuery}},t={};function n(i){var r=t[i];if(void 0!==r)return r.exports;var o=t[i]={exports:{}};return e[i](o,o.exports,n),o.exports}!function(){var e=u(n(754)),t=u(n(196)),i=u(n(363)),r=n(691),o=n(939),a=n(624),l=u(n(311)),s=u(n(265)),d=n(595),c=n(648);function u(e){return e&&e.__esModule?e:{default:e}}const p="sslinkinternal";t.default.addAction("sslink",{text:e.default._t("CMS.LINKLABEL_PAGE","Page on this site"),onAction:e=>e.execCommand(p),priority:90},editorIdentifier).addCommandWithUrlTest(p,/^\[sitetree_link.+]$/);const f={init(e){e.addCommand(p,(()=>{(0,l.default)(`#${e.id}`).entwine("ss").openLinkInternalDialog()}))}},g="insert-link__dialog-wrapper--internal",h=(0,c.provideInjector)((0,d.createInsertLinkModal)("SilverStripe\\CMS\\Controllers\\CMSPageEditController","editorInternalLink"));l.default.entwine("ss",(t=>{t("textarea.htmleditor").entwine({openLinkInternalDialog(){let e=t(`#${g}`);e.length||(e=t(`<div id="${g}" />`),t("body").append(e)),e.addClass("insert-link__dialog-wrapper"),e.setElement(this),e.open()}}),t(`#${g}`).entwine({ReactRoot:null,renderModal(t){var n=this;const l=ss.store,s=ss.apolloClient,d=this.getOriginalAttributes(),c=this.getRequireLinkText();let u=this.getReactRoot();u||(u=(0,r.createRoot)(this[0]),this.setReactRoot(u)),u.render(i.default.createElement(o.ApolloProvider,{client:s},i.default.createElement(a.Provider,{store:l},i.default.createElement(h,{isOpen:t,onInsert:function(){return n.handleInsert(...arguments)},onClosed:()=>this.close(),title:e.default._t("CMS.LINK_PAGE","Link to a page"),bodyClassName:"modal__dialog",className:"insert-link__dialog-wrapper--internal",fileAttributes:d,identifier:"Admin.InsertLinkInternalModal",requireLinkText:c}))))},buildAttributes(e){return{href:`${s.default.serialise({name:"sitetree_link",properties:{id:e.PageID}},!0)}${e.Anchor&&e.Anchor.length?`#${e.Anchor}`:""}`,target:e.TargetBlank?"_blank":"",title:e.Description}},getOriginalAttributes(){const e=this.getElement().getEditor(),n=t(e.getSelectedNode()),i=(n.attr("href")||"").split("#");if(!i[0])return{};const r=s.default.match("sitetree_link",!1,i[0]);return r?{PageID:r.properties.id?parseInt(r.properties.id,10):0,Anchor:i[1]||"",Description:n.attr("title"),TargetBlank:!!n.attr("target")}:{}}})})),tinymce.PluginManager.add(p,(e=>f.init(e)))}()}();
\ No newline at end of file
diff --git a/client/src/legacy/TinyMCE_sslink-anchor.js b/client/src/legacy/TinyMCE_sslink-anchor.js
index 7ade0bc9..f1d95a1f 100644
--- a/client/src/legacy/TinyMCE_sslink-anchor.js
+++ b/client/src/legacy/TinyMCE_sslink-anchor.js
@@ -76,11 +76,7 @@ jQuery.entwine('ss', ($) => {
       const handleHide = () => this.close();
       const handleInsert = (...args) => this.handleInsert(...args);
       const attrs = this.getOriginalAttributes();
-      const editor = this.getElement().getEditor();
-      const selection = editor.getInstance().selection;
-      const selectionContent = editor.getSelection();
-      const tagName = selection.getNode().tagName;
-      const requireLinkText = tagName !== 'A' && selectionContent.trim() === '';
+      const requireLinkText = this.getRequireLinkText();
       const currentPageID = Number($('#Form_EditForm_ID').val() || 0);
 
       // create/update the react component
diff --git a/client/src/legacy/TinyMCE_sslink-internal.js b/client/src/legacy/TinyMCE_sslink-internal.js
index 83aaa57c..d34c6545 100644
--- a/client/src/legacy/TinyMCE_sslink-internal.js
+++ b/client/src/legacy/TinyMCE_sslink-internal.js
@@ -95,22 +95,6 @@ jQuery.entwine('ss', ($) => {
       );
     },
 
-    /**
-     * Determine whether to show the link text field
-     *
-     * @return {Boolean}
-     */
-    getRequireLinkText() {
-      const editor = this.getElement().getEditor();
-      const selection = editor.getInstance().selection;
-      const selectionContent = editor.getSelection();
-
-      const tagName = selection.getNode().tagName;
-      const requireLinkText = tagName !== 'A' && selectionContent.trim() === '';
-
-      return requireLinkText;
-    },
-
     /**
      * @param {Object} data - Posted data
      * @return {Object}
diff --git a/tests/behat/features/insert-a-link.feature b/tests/behat/features/insert-a-link.feature
index d260e5d2..d49d086a 100644
--- a/tests/behat/features/insert-a-link.feature
+++ b/tests/behat/features/insert-a-link.feature
@@ -25,6 +25,19 @@ So that I can link to a external website or a page on my site
     # Required to avoid "unsaved changes" browser dialog
     Then I press the "Save" button
 
+  Scenario: I can wrap an image in a link to an internal page
+    Given I fill in the "Content" HTML field with "<p><img src='file1.jpg'></p>"
+    When I select the image "file1.jpg" in the "Content" HTML field
+      And I press the "Insert link" HTML field button
+      And I click "Page on this site" in the ".tox-collection__group" element
+    Then I should see an "form#Form_editorInternalLink" element
+      And I should not see "Link text"
+    When I select "About Us" in the "#Form_editorInternalLink_PageID_Holder" tree dropdown
+      And I press the "Insert link" button
+    Then the "Content" HTML field should contain "<a href="[sitetree_link,id=2]"><img src="file1.jpg"></a>"
+      # Required to avoid "unsaved changed" browser dialog
+      And I press the "Save" button
+
   Scenario: I can edit a link to an internal page
     Given I fill in the "Content" HTML field with "<a title='my desc' href='[sitetree_link,id=2]'>awesome</a>"
       And I select "awesome" in the "Content" HTML field
@@ -53,6 +66,19 @@ So that I can link to a external website or a page on my site
     # Required to avoid "unsaved changes" browser dialog
     Then I press the "Save" button
 
+  Scenario: I can wrap an image in a link to an external URL
+    Given I fill in the "Content" HTML field with "<p><img src='file1.jpg'></p>"
+    When I select the image "file1.jpg" in the "Content" HTML field
+      And I press the "Insert link" HTML field button
+    When I click "Link to external URL" in the ".tox-collection__group" element
+      And I should see an "form#Form_ModalsEditorExternalLink" element
+      And I should not see "Link text"
+    When I fill in "http://silverstripe.org" for "URL"
+      And I press the "Insert link" button
+    Then the "Content" HTML field should contain "<a href="http://silverstripe.org"><img src="file1.jpg"></a>"
+      # Required to avoid "unsaved changed" browser dialog
+      And I press the "Save" button
+
   Scenario: I can edit a link
     Given I fill in the "Content" HTML field with "<p>My <a href='http://silverstripe.org'>awesome</a> content"
       And I select "awesome" in the "Content" HTML field
diff --git a/tests/behat/features/insert-anchor-link.feature b/tests/behat/features/insert-anchor-link.feature
index f6e5380e..193a5614 100644
--- a/tests/behat/features/insert-anchor-link.feature
+++ b/tests/behat/features/insert-anchor-link.feature
@@ -29,6 +29,21 @@ So that I can link to a external website or a page on my site
     # Required to avoid "unsaved changes" browser dialog
     Then I press the "Save" button
 
+  Scenario: I can wrap an image in a link to an anchor in an internal page
+    Given I fill in the "Content" HTML field with "<p><img src='file1.jpg'></p>"
+    When I select the image "file1.jpg" in the "Content" HTML field
+      And I press the "Insert link" HTML field button
+      And I click "Anchor on a page" in the ".tox-collection__group" element
+    Then I should see an "form#Form_editorAnchorLink" element
+      And I should not see "Link text"
+      And I should see "About Us" in the "#Form_editorAnchorLink_PageID_Holder .treedropdownfield__value-container" element
+    When I select "Details" in the "#Form_editorAnchorLink_PageID_Holder" tree dropdown
+      And I select "youranchor" in the "#Form_editorAnchorLink_Anchor_Holder" anchor dropdown
+      And I press the "Insert link" button
+    Then the "Content" HTML field should contain "<a href="[sitetree_link,id=3]#youranchor"><img src="file1.jpg"></a>"
+      # Required to avoid "unsaved changed" browser dialog
+      And I press the "Save" button
+
   Scenario: I can link to an anchor from a dataobject on the current page
     When I select "awesome" in the "Content" HTML field
       And I press the "Insert link" HTML field button