diff --git a/app/workers/import/jira_create_project_job/custom_field_names.rb b/app/workers/import/jira_create_project_job/custom_field_names.rb
index 4bfd03a77fed..d7e129f26802 100644
--- a/app/workers/import/jira_create_project_job/custom_field_names.rb
+++ b/app/workers/import/jira_create_project_job/custom_field_names.rb
@@ -30,6 +30,9 @@
 module Import
   class JiraCreateProjectJob
     module CustomFieldNames
+      # The counter `unique_name` appends when a name is taken and cannot be reused (e.g. int vs float type of the field)
+      NUMBERING_SUFFIX = /\s*\(\d+\)\z/
+
       module_function
 
       # Matches `Example`, `Example (2)`, `Example (DYX)` and `Example (DYX, ABC)
@@ -41,6 +44,14 @@ def candidates(base_name)
           .order(:id)
       end
 
+      def same_field?(custom_field_name, import_name)
+        without_numbering(custom_field_name).casecmp?(import_name.to_s)
+      end
+
+      def without_numbering(name)
+        name.to_s.sub(NUMBERING_SUFFIX, "")
+      end
+
       def unique_name(name)
         unique_name = name
         suffix = 2
diff --git a/app/workers/import/jira_create_project_job/jira_import_custom_field_builder.rb b/app/workers/import/jira_create_project_job/jira_import_custom_field_builder.rb
index f9146007fa9e..2416f224aad8 100644
--- a/app/workers/import/jira_create_project_job/jira_import_custom_field_builder.rb
+++ b/app/workers/import/jira_create_project_job/jira_import_custom_field_builder.rb
@@ -299,8 +299,19 @@ def compatible_multi_value?(custom_field)
       def best_matching_candidate(candidates, run_custom_field_ids)
         return best_value_bearing_candidate(candidates, run_custom_field_ids) if value_bearing_format?
 
-        candidates.find { |cf| cf.name.casecmp?(@import_name) } ||
-          candidates.find { |cf| cf.name.casecmp?(stable_base_name) }
+        exact_name_match(candidates) || numbered_name_match(candidates)
+      end
+
+      def exact_name_match(candidates)
+        import_names.filter_map { |name| candidates.find { |cf| cf.name.casecmp?(name) } }.first
+      end
+
+      def numbered_name_match(candidates)
+        import_names.filter_map { |name| candidates.find { |cf| CustomFieldNames.same_field?(cf.name, name) } }.first
+      end
+
+      def import_names
+        [@import_name, stable_base_name].uniq
       end
 
       def value_bearing_format?
diff --git a/docs/installation-and-operations/jira-migration/custom-fields/README.md b/docs/installation-and-operations/jira-migration/custom-fields/README.md
index 6ad5fa4883ab..75eaf11b9939 100644
--- a/docs/installation-and-operations/jira-migration/custom-fields/README.md
+++ b/docs/installation-and-operations/jira-migration/custom-fields/README.md
@@ -141,6 +141,9 @@ If an OpenProject custom field with the same name and format already exists (fro
 the migrator reuses it instead of creating a duplicate. The existing custom field is linked to the import and its values are preserved.
 
 If a name collision exists but the formats differ, the migrator appends a numeric suffix to the new field name (e.g., `My Field (2)`).
+Such a numeric suffix is disregarded when the migrator looks for a field to reuse, so a later run reuses `My Field (2)`
+instead of creating `My Field (3)`. Only a numeric suffix is treated this way - the project-key suffixes described under
+[Field contexts](#field-contexts) stay part of the name.
 
 For **Hierarchy** and **List** fields, deduplication is attempted but not guaranteed because option lists may differ. 
 A new custom field with a numeric suffix may be created for these types.
diff --git a/spec/workers/import/jira_create_project_job/custom_field_names_spec.rb b/spec/workers/import/jira_create_project_job/custom_field_names_spec.rb
index 84acb4e6c915..4990790d7f38 100644
--- a/spec/workers/import/jira_create_project_job/custom_field_names_spec.rb
+++ b/spec/workers/import/jira_create_project_job/custom_field_names_spec.rb
@@ -65,6 +65,38 @@
     end
   end
 
+  describe ".same_field?" do
+    it "matches the same name regardless of case" do
+      expect(described_class).to be_same_field("Story Points", "STORY POINTS")
+    end
+
+    it "matches a stored name carrying the counter unique_name appends" do
+      expect(described_class).to be_same_field("Story Points (2)", "Story Points")
+      expect(described_class).to be_same_field("Story Points (12)", "Story Points")
+    end
+
+    it "strips the counter from the stored name only" do
+      expect(described_class).not_to be_same_field("Story Points", "Story Points (2)")
+    end
+
+    it "matches a Jira field whose own name ends in a number against its renamed field" do
+      expect(described_class).to be_same_field("Story Points (2) (2)", "Story Points (2)")
+    end
+
+    it "keeps a project key suffix apart from the counter" do
+      expect(described_class).not_to be_same_field("Story Points (XYZ)", "Story Points")
+    end
+
+    it "matches a project key suffix with itself despite a counter" do
+      expect(described_class).to be_same_field("Story Points (XYZ) (2)", "Story Points (XYZ)")
+    end
+
+    it "does not match a different name" do
+      expect(described_class).not_to be_same_field("Story Points Estimate", "Story Points")
+      expect(described_class).not_to be_same_field("Story Points 2", "Story Points")
+    end
+  end
+
   describe ".unique_name" do
     subject(:unique_name) { described_class.unique_name("Resolution") }
 
diff --git a/spec/workers/import/jira_create_project_job/jira_import_custom_field_builder_spec.rb b/spec/workers/import/jira_create_project_job/jira_import_custom_field_builder_spec.rb
index 30fbfb1e8152..63fc61004d6d 100644
--- a/spec/workers/import/jira_create_project_job/jira_import_custom_field_builder_spec.rb
+++ b/spec/workers/import/jira_create_project_job/jira_import_custom_field_builder_spec.rb
@@ -981,21 +981,41 @@ def date_builder
         expect(date_builder.find_existing_custom_field).to eq(exact)
       end
 
-      it "does not reuse a suffixed candidate when no exact name matches" do
-        create(:date_wp_custom_field, name: "Due (archived)")
+      it "prefers the exact base name over a numbered candidate created before it" do
         create(:date_wp_custom_field, name: "Due (2)")
+        exact = create(:date_wp_custom_field, name: "Due")
+
+        expect(date_builder.find_existing_custom_field).to eq(exact)
+      end
+
+      it "reuses the numbered field an earlier run created when no exact name matches" do
+        create(:date_wp_custom_field, name: "Due (archived)")
+        numbered = create(:date_wp_custom_field, name: "Due (2)")
+
+        expect(date_builder.find_existing_custom_field).to eq(numbered)
+      end
+
+      it "ignores a candidate whose suffix is not the counter unique_name appends" do
+        create(:date_wp_custom_field, name: "Due (archived)")
 
         expect(date_builder.find_existing_custom_field).to be_nil
       end
 
-      it "keeps two Jira fields apart when one is named like the other's dedup suffix" do
-        suffixed = create(:string_wp_custom_field, name: "foo (2)")
-        schema = { "type" => "string", "custom" => "com.atlassian.jira.plugin.system.customfieldtypes:textfield" }
-        builder = described_class.new(jira_field_for(name: "foo", schema:), jira_import:)
+      it "reuses the renamed field of a Jira field whose own name ends in a number" do
+        create(:string_wp_custom_field, name: "Due (2)")
+        renamed = create(:date_wp_custom_field, name: "Due (2) (2)")
+        schema = { "type" => "date", "custom" => "com.atlassian.jira.plugin.system.customfieldtypes:datepicker" }
+        builder = described_class.new(jira_field_for(name: "Due (2)", schema:), jira_import:)
+
+        expect(builder.find_existing_custom_field).to eq(renamed)
+      end
+
+      it "does not let a Jira field whose name ends in a number take over the plain field" do
+        create(:date_wp_custom_field, name: "Due")
+        schema = { "type" => "date", "custom" => "com.atlassian.jira.plugin.system.customfieldtypes:datepicker" }
+        builder = described_class.new(jira_field_for(name: "Due (2)", schema:), jira_import:)
 
         expect(builder.find_existing_custom_field).to be_nil
-        expect(builder.custom_field_settings.first).to eq("foo")
-        expect(suffixed.reload.name).to eq("foo (2)")
       end
     end
 
diff --git a/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb b/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb
index 95849b754afc..f02836220470 100644
--- a/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb
+++ b/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb
@@ -1384,4 +1384,61 @@ def per_issue_union(job, registry, jira_project)
       end
     end
   end
+
+  describe "a custom field an earlier import run had to name with a counter" do
+    let!(:jira_field) do
+      create(:jira_field, jira_import:,
+                          origin_id: "customfield_10254",
+                          payload: {
+                            "id" => "customfield_10254",
+                            "name" => "CF Number",
+                            "schema" => {
+                              "type" => "number",
+                              "custom" => "com.atlassian.jira.plugin.system.customfieldtypes:float",
+                              "customId" => 10254
+                            }
+                          })
+    end
+    let!(:jira_issue) do
+      create(:jira_issue, jira_import:,
+                          origin_id: "10200",
+                          jira_project:,
+                          payload: issue_payload)
+    end
+
+    # An existing field of an incompatible format cannot be reused, so the first run has to fall
+    # back to the next free name.
+    let!(:incompatible_custom_field) { create(:integer_wp_custom_field, name: "CF Number") }
+
+    let(:second_jira_import) do
+      create(:jira_import, jira:, author:,
+                           projects: [{ "id" => jira_project_id, "key" => jira_project_key,
+                                        "name" => jira_project_name }])
+    end
+
+    def run_second_import
+      second_jira_project = create(:jira_project, jira_import: second_jira_import,
+                                                  origin_id: jira_project_id,
+                                                  payload: jira_project_payload)
+      create(:jira_field, jira_import: second_jira_import,
+                          origin_id: jira_field.origin_id,
+                          payload: jira_field.payload)
+      create(:jira_issue, jira_import: second_jira_import,
+                          origin_id: "10200",
+                          jira_project: second_jira_project,
+                          payload: issue_payload)
+      Import::JiraCreateCustomFieldsJob.perform_now(second_jira_import.id)
+    end
+
+    before { import_project }
+
+    it "names it with the next free counter" do
+      expect(WorkPackageCustomField.pluck(:name)).to contain_exactly("CF Number", "CF Number (2)")
+    end
+
+    it "reuses it on a later import run instead of allocating the next counter" do
+      expect { run_second_import }.not_to change(WorkPackageCustomField, :count)
+      expect(WorkPackageCustomField.pluck(:name)).to contain_exactly("CF Number", "CF Number (2)")
+    end
+  end
 end